JPH0971557A - Amino group-containing benzoic ester derivative - Google Patents
Amino group-containing benzoic ester derivativeInfo
- Publication number
- JPH0971557A JPH0971557A JP7228730A JP22873095A JPH0971557A JP H0971557 A JPH0971557 A JP H0971557A JP 7228730 A JP7228730 A JP 7228730A JP 22873095 A JP22873095 A JP 22873095A JP H0971557 A JPH0971557 A JP H0971557A
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydroxybenzoic acid
- methyl
- ethyl
- aminoethyl ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 benzoic ester Chemical class 0.000 title claims abstract description 27
- 125000003277 amino group Chemical group 0.000 title claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract description 157
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 abstract description 78
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001414 amino alcohols Chemical class 0.000 abstract description 7
- 238000005859 coupling reaction Methods 0.000 abstract description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 150000008049 diazo compounds Chemical class 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 3
- 125000006239 protecting group Chemical group 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 description 65
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- AQSCHALQLXXKKC-UHFFFAOYSA-N 4-phenylmethoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCC1=CC=CC=C1 AQSCHALQLXXKKC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 2
- QGNLHMKIGMZKJX-UHFFFAOYSA-N 3-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(Cl)=C1 QGNLHMKIGMZKJX-UHFFFAOYSA-N 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- LTFHNKUKQYVHDX-UHFFFAOYSA-N 4-hydroxy-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1O LTFHNKUKQYVHDX-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- CGEOYYBCLBIBLG-UHFFFAOYSA-N (4-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C(Cl)=O)C=C1 CGEOYYBCLBIBLG-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 description 1
- BBMFSGOFUHEVNP-UHFFFAOYSA-N 4-hydroxy-2-methylbenzoic acid Chemical compound CC1=CC(O)=CC=C1C(O)=O BBMFSGOFUHEVNP-UHFFFAOYSA-N 0.000 description 1
- ICEKEZSKMGHZNT-UHFFFAOYSA-N 4-phenylmethoxybenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OCC1=CC=CC=C1 ICEKEZSKMGHZNT-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 229940114055 beta-resorcylic acid Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000001632 sodium acetate Chemical group 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は医薬、農薬の中間体
もしくは感熱記録材料の添加剤として有用な新規なアミ
ノ基含有安息香酸エステル誘導体に関する。TECHNICAL FIELD The present invention relates to a novel amino group-containing benzoic acid ester derivative which is useful as an intermediate for medicines, agricultural chemicals or an additive for heat-sensitive recording materials.
【０００２】[0002]
【従来の技術】ジアゾ感熱記録材料のカップリング反応
促進剤、もしくは電子供与性無色染料を用いた発色体の
消色剤として現在までに種々の塩基性物質が検討されて
おり、代表的なものとしては、第３級アミン類、ピペリ
ジン類、ピペラジン類、アミジン類、フォルムアミジン
類、ピリジン類、グアニジン類、モルホリン類等の含窒
素化合物が挙げられる。近年、ジアゾ化合物を用いた感
熱記録材料、電子供与性無色染料の発色体を用いた感熱
記録材料等において使用前の保存性と記録速度の速い記
録材料を作成する試みが成されているが、未だ充分満足
のできるレベルに達していないのが現状であり、特に記
録材料の高感度化の点からジアゾ化合物のカップリング
反応及び発色体の消色反応のさらなる反応性向上が必要
とされている。この問題を解決する目的で本発明者らは
鋭意検討した結果、分子内にフェノール性水酸基を有す
る化合物が優れた性能を示すことを見出し本発明に至っ
た。2. Description of the Related Art Various basic substances have been studied so far as a coupling reaction accelerator of a diazo heat-sensitive recording material or a decoloring agent of a color former using an electron-donating colorless dye, and typical ones have been studied so far. Examples thereof include nitrogen-containing compounds such as tertiary amines, piperidines, piperazines, amidines, formamidines, pyridines, guanidines and morpholines. In recent years, attempts have been made to prepare a recording material having a high preservability and a high recording speed before use in a thermal recording material using a diazo compound, a thermal recording material using a color former of an electron-donating colorless dye, and the like. At present, it has not reached a sufficiently satisfactory level, and further improvement in reactivity of the coupling reaction of the diazo compound and the decolorization reaction of the color-developing substance is required especially from the viewpoint of high sensitivity of the recording material. . As a result of intensive studies made by the present inventors for the purpose of solving this problem, they have found that a compound having a phenolic hydroxyl group in the molecule exhibits excellent performance, and arrived at the present invention.
【０００３】[0003]
【発明が解決しようとする課題】従って、本発明の目的
は、ジアゾ化合物のカップリング反応促進、もしくは電
子供与性無色染料を用いた発色体の消色促進剤として有
効な化合物を提供することにある。Therefore, an object of the present invention is to provide a compound which is effective as an accelerator for accelerating a coupling reaction of a diazo compound, or as an erasing accelerator for a color developing material using an electron donating colorless dye. is there.
【０００４】[0004]
【課題を解決するための手段】本発明の目的は、一般式
（Ｉ）で示されるアミノ基含有安息香酸エステル誘導体
によって達成された。 一般式（Ｉ）The object of the present invention has been achieved by an amino group-containing benzoic acid ester derivative represented by the general formula (I). General formula (I)
【０００５】[0005]
【化２】 Embedded image
【０００６】式中、Ｒ1 は炭素数１〜６の直鎖もしくは
分岐のアルキル基を示し、Ａｒはアリール基を示し、ｍ
は２〜６の整数を示し、ｎは２〜９の整数を示し、Ｘは
水素原子、ハロゲン原子、水酸基、低級アルキル基、低
級アルコキシ基を示す。In the formula, R 1 represents a linear or branched alkyl group having 1 to 6 carbon atoms, Ar represents an aryl group, and m
Represents an integer of 2 to 6, n represents an integer of 2 to 9, and X represents a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group or a lower alkoxy group.
【０００７】一般式（Ｉ）においてＲ1 で表される基と
しては、メチル基、エチル基、ｎ−プロピル基、iso-プ
ロピル基、ｎ−ブチル基、iso-ブチル基、ｎ−ペンチル
基、ｎ−ヘキシル基などが挙げられ、好ましくはメチル
基、エチル基、ｎ−プロピル基、iso-プロピル基が挙げ
られる。一般式（Ｉ）においてＡｒで表されるアリール
基としては、フェニル基、ナフチル基などが挙げられ、
これらのアリール基はハロゲン原子、炭素数１〜４のア
ルキル基、炭素数１〜４のアルコキシ基などで置換され
ていてもよい。これらアリール基の例としてはフェニル
基、２−クロロフェニル基、３−クロロフェニル基、４
−クロロフェニル基、２−フルオロフェニル基、３−フ
ルオロフェニル基、４−フルオロフェニル基、２−トリ
ル基、３−トリル基、４−トリル基、２−エチルフェニ
ル基、３−エチルフェニル基、４−エチルフェニル基、
４−ｎ−プロピルフェニル基、２−メトキシフェニル
基、３−メトキシフェニル基、４−メトキシフェニル
基、２−エトキシフェニル基、３−エトキシフェニル
基、４−エトキシフェニル基、４−ｎ−プロポキシフェ
ニル基、１−ナフチル基、２−ナフチル基、４−メトキ
シ−１−ナフチル基、４−エトキシ−１−ナフチル基、
４−ｎ−プロポキシ−１−ナフチル基、６−メトキシ−
２−ナフチル基、６−エトキシ−２−ナフチル基、６−
ｎ−プロポキシ−２−ナフチル基などが挙げられ、好ま
しくはフェニル基、２−クロロフェニル基、４−クロロ
フェニル基、４−フルオロフェニル基、２−トリル基、
３−トリル基、４−トリル基、２−エチルフェニル基、
４−エチルフェニル基、２−メトキシフェニル基、３−
メトキシフェニル基、４−メトキシフェニル基、４−エ
トキシフェニル基が挙げられる。Examples of the group represented by R 1 in the general formula (I) include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, n-pentyl group, Examples thereof include an n-hexyl group, and preferably a methyl group, an ethyl group, an n-propyl group and an iso-propyl group. Examples of the aryl group represented by Ar in the general formula (I) include a phenyl group and a naphthyl group,
These aryl groups may be substituted with a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or the like. Examples of these aryl groups include phenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4
-Chlorophenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-tolyl group, 3-tolyl group, 4-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4 -Ethylphenyl group,
4-n-propylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-ethoxyphenyl group, 3-ethoxyphenyl group, 4-ethoxyphenyl group, 4-n-propoxyphenyl Group, 1-naphthyl group, 2-naphthyl group, 4-methoxy-1-naphthyl group, 4-ethoxy-1-naphthyl group,
4-n-propoxy-1-naphthyl group, 6-methoxy-
2-naphthyl group, 6-ethoxy-2-naphthyl group, 6-
and n-propoxy-2-naphthyl group and the like, and preferably phenyl group, 2-chlorophenyl group, 4-chlorophenyl group, 4-fluorophenyl group, 2-tolyl group,
3-tolyl group, 4-tolyl group, 2-ethylphenyl group,
4-ethylphenyl group, 2-methoxyphenyl group, 3-
Examples thereof include a methoxyphenyl group, a 4-methoxyphenyl group, and a 4-ethoxyphenyl group.
【０００８】一般式（Ｉ）において−Ｃm Ｈ2m−で表さ
れる連結基としては以下に示す構造が挙げられる。[0008] -C m H 2m in the general Formulas (I) - as the linking group represented by include the structures shown below.
【０００９】[0009]
【化３】 Embedded image
【００１０】好ましくは以下に示す構造が挙げられる。The following structures are preferable.
【００１１】[0011]
【化４】 Embedded image
【００１２】一般式（Ｉ）において−Ｃn Ｈ2n−で表さ
れる連結基としては以下に示す構造が挙げられる。Examples of the linking group represented by —C n H 2n — in the general formula (I) include the structures shown below.
【００１３】[0013]
【化５】 Embedded image
【００１４】好ましくは以下に示す構造が挙げられる。The following structures are preferred.
【００１５】[0015]
【化６】 [Chemical 6]
【００１６】一般式（Ｉ）においてＸで表される基とし
ては水素原子、塩素原子、フッ素原子、水酸基、メチル
基、エチル基、プロピル基、ブチル基、メトキシ基、エ
トキシ基、プロポキシ基等が挙げられ、好ましくは水素
原子、塩素原子、水酸基、メチル基、メトキシ基が挙げ
られる。以下に一般式（Ｉ）で表される本発明の化合物
の具体例を示す。Examples of the group represented by X in the general formula (I) include hydrogen atom, chlorine atom, fluorine atom, hydroxyl group, methyl group, ethyl group, propyl group, butyl group, methoxy group, ethoxy group, propoxy group and the like. Of these, hydrogen atom, chlorine atom, hydroxyl group, methyl group and methoxy group are preferable. Specific examples of the compound of the present invention represented by formula (I) are shown below.
【００１７】４−ヒドロキシ安息香酸 ２−Ｎ−メチル
−Ｎ−（２−フェノキシエチル）アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（２−クロロフェノキシ）エチル〕アミノエチルエステ
ル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（３−クロロフェノキシ）エチル〕アミノエチルエステ
ル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（４−クロロフェノキシ）エチル〕アミノエチルエステ
ル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（４−フルオロフェノキシ）エチル〕アミノエチルエス
テル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（２−メチルフェノキシ）エチル〕アミノエチルエステ
ル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（３−メチルフェノキシ）エチル〕アミノエチルエステ
ル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（４−メチルフェノキシ）エチル〕アミノエチルエステ
ル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（４−エチルフェノキシ）エチル〕アミノエチルエステ
ル4-Hydroxybenzoic acid 2-N-methyl-N- (2-phenoxyethyl) aminoethyl ester 4-Hydroxybenzoic acid 2-N-methyl-N- [2-
(2-Chlorophenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(3-Chlorophenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(4-Chlorophenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(4-Fluorophenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(2-Methylphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(3-Methylphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(4-Methylphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(4-Ethylphenoxy) ethyl] aminoethyl ester
【００１８】４−ヒドロキシ安息香酸 ２−Ｎ−メチル
−Ｎ−〔２−（２−メトキシフェノキシ）エチル〕アミ
ノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（３−メトキシフェノキシ）エチル〕アミノエチルエス
テル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（４−メトキシフェノキシ）エチル〕アミノエチルエス
テル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（４−エトキシフェノキシ）エチル〕アミノエチルエス
テル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（４−ｎ−プロポキシフェノキシ）エチル〕アミノエチ
ルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（１−ナフチルオキシ）エチル〕アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（２−ナフチルオキシ）エチル〕アミノエチルエステル4-Hydroxybenzoic acid 2-N-methyl-N- [2- (2-methoxyphenoxy) ethyl] aminoethyl ester 4-Hydroxybenzoic acid 2-N-methyl-N- [2-
(3-Methoxyphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(4-Methoxyphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(4-Ethoxyphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(4-n-Propoxyphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(1-Naphthyloxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(2-Naphthyloxy) ethyl] aminoethyl ester
【００１９】４−ヒドロキシ安息香酸 ２−Ｎ−メチル
−Ｎ−〔２−フェノキシ−１−メチルエチル〕アミノエ
チルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（４−クロロフェノキシ）−１−メチルエチル〕アミノ
エチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（４−メチルフェノキシ）−１−メチルエチル〕アミノ
エチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−〔２−
（４−メトキシフェノキシ）−１−メチルエチル〕アミ
ノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−（３−
フェノキシプロピル）アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−（６−
フェノキシヘキシル）アミノエチルエステル ４−ヒドロキシ安息香酸 ３−Ｎ−メチル−Ｎ−（２−
フェノキシエチル）アミノプロピルエステル ４−ヒドロキシ安息香酸 ６−Ｎ−メチル−Ｎ−（２−
フェノキシエチル）アミノヘキシルエステル ４−ヒドロキシ安息香酸 ９−Ｎ−メチル−Ｎ−（２−
フェノキシエチル）アミノノニルエステル ３−クロロ−４−ヒドロキシ安息香酸 ２−Ｎ−メチル
−Ｎ−（２−フェノキシエチル）アミノエチルエステル ２−メチル−４−ヒドロキシ安息香酸 ２−Ｎ−メチル
−Ｎ−（２−フェノキシエチル）アミノエチルエステル ３−メチル−４−ヒドロキシ安息香酸 ２−Ｎ−メチル
−Ｎ−（２−フェノキシエチル）アミノエチルエステル ３−メトキシ−４−ヒドロキシ安息香酸 ２−Ｎ−メチ
ル−Ｎ−（２−フェノキシエチル）アミノエチルエステ
ル ２，４−ジヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−
（２−フェノキシエチル）アミノエチルエステル ３，４−ジヒドロキシ安息香酸 ２−Ｎ−メチル−Ｎ−
（２−フェノキシエチル）アミノエチルエステル4-Hydroxybenzoic acid 2-N-methyl-N- [2-phenoxy-1-methylethyl] aminoethyl ester 4-Hydroxybenzoic acid 2-N-methyl-N- [2-
(4-Chlorophenoxy) -1-methylethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(4-Methylphenoxy) -1-methylethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- [2-
(4-Methoxyphenoxy) -1-methylethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- (3-
Phenoxypropyl) aminoethyl ester 4-hydroxybenzoic acid 2-N-methyl-N- (6-
Phenoxyhexyl) aminoethyl ester 4-hydroxybenzoic acid 3-N-methyl-N- (2-
Phenoxyethyl) aminopropyl ester 4-hydroxybenzoic acid 6-N-methyl-N- (2-
Phenoxyethyl) aminohexyl ester 4-hydroxybenzoic acid 9-N-methyl-N- (2-
Phenoxyethyl) aminononyl ester 3-chloro-4-hydroxybenzoic acid 2-N-methyl-N- (2-phenoxyethyl) aminoethyl ester 2-methyl-4-hydroxybenzoic acid 2-N-methyl-N- ( 2-phenoxyethyl) aminoethyl ester 3-methyl-4-hydroxybenzoic acid 2-N-methyl-N- (2-phenoxyethyl) aminoethyl ester 3-methoxy-4-hydroxybenzoic acid 2-N-methyl-N -(2-phenoxyethyl) aminoethyl ester 2,4-dihydroxybenzoic acid 2-N-methyl-N-
(2-phenoxyethyl) aminoethyl ester 3,4-dihydroxybenzoic acid 2-N-methyl-N-
(2-phenoxyethyl) aminoethyl ester
【００２０】４−ヒドロキシ安息香酸 ２−Ｎ−エチル
−Ｎ−（２−フェノキシエチル）アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−エチル−Ｎ−〔２−
（４−クロロフェノキシ）エチル〕アミノエチルエステ
ル ４−ヒドロキシ安息香酸 ２−Ｎ−エチル−Ｎ−〔２−
（４−メチルフェノキシ）エチル〕アミノエチルエステ
ル ４−ヒドロキシ安息香酸 ２−Ｎ−エチル−Ｎ−〔２−
（４−メトキシフェノキシ）エチル〕アミノエチルエス
テル ４−ヒドロキシ安息香酸 ２−Ｎ−エチル−Ｎ−〔２−
（４−エトキシフェノキシ）エチル〕アミノエチルエス
テル ４−ヒドロキシ安息香酸 ２−Ｎ−エチル−Ｎ−〔２−
フェノキシ−１−メチルエチル〕アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−エチル−Ｎ−〔２−
（４−クロロフェノキシ）−１−メチルエチル〕アミノ
エチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−エチル−Ｎ−〔２−
（４−メチルフェノキシ）−１−メチルエチル〕アミノ
エチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−エチル−Ｎ−〔２−
（４−メトキシフェノキシ）−１−メチルエチル〕アミ
ノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−エチル−Ｎ−（３−
フェノキシプロピル）アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−エチル−Ｎ−（６−
フェノキシヘキシル）アミノエチルエステル ４−ヒドロキシ安息香酸 ３−Ｎ−エチル−Ｎ−（２−
フェノキシエチル）アミノプロピルエステル ４−ヒドロキシ安息香酸 ６−Ｎ−エチル−Ｎ−（２−
フェノキシエチル）アミノヘキシルエステル ４−ヒドロキシ安息香酸 ９−Ｎ−エチル−Ｎ−（２−
フェノキシエチル）アミノノニルエステル4-Hydroxybenzoic acid 2-N-ethyl-N- (2-phenoxyethyl) aminoethyl ester 4-Hydroxybenzoic acid 2-N-ethyl-N- [2-
(4-Chlorophenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-ethyl-N- [2-
(4-Methylphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-ethyl-N- [2-
(4-Methoxyphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-ethyl-N- [2-
(4-Ethoxyphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-ethyl-N- [2-
Phenoxy-1-methylethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-ethyl-N- [2-
(4-Chlorophenoxy) -1-methylethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-ethyl-N- [2-
(4-Methylphenoxy) -1-methylethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-ethyl-N- [2-
(4-Methoxyphenoxy) -1-methylethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-ethyl-N- (3-
Phenoxypropyl) aminoethyl ester 4-hydroxybenzoic acid 2-N-ethyl-N- (6-
Phenoxyhexyl) aminoethyl ester 4-hydroxybenzoic acid 3-N-ethyl-N- (2-
Phenoxyethyl) aminopropyl ester 4-hydroxybenzoic acid 6-N-ethyl-N- (2-
Phenoxyethyl) aminohexyl ester 4-hydroxybenzoic acid 9-N-ethyl-N- (2-
Phenoxyethyl) aminononyl ester
【００２１】４−ヒドロキシ安息香酸 ２−Ｎ−ｎ−プ
ロピル−Ｎ−（２−フェノキシエチル）アミノエチルエ
ステル ４−ヒドロキシ安息香酸 ２−Ｎ−ｎ−プロピル−Ｎ−
〔２−（４−クロロフェノキシ）エチル〕アミノエチル
エステル ４−ヒドロキシ安息香酸 ２−Ｎ−ｎ−プロピル−Ｎ−
〔２−（４−メチルフェノキシ）エチル〕アミノエチル
エステル ４−ヒドロキシ安息香酸 ２−Ｎ−ｎ−プロピル−Ｎ−
〔２−（４−メトキシフェノキシ）エチル〕アミノエチ
ルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−ｎ−プロピル−Ｎ−
（２−フェノキシ−１−メチルエチル）アミノエチルエ
ステル ４−ヒドロキシ安息香酸 ２−Ｎ−ｎ−プロピル−Ｎ−
〔２−（４−クロロフェノキシ）−１−メチルエチル〕
アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−ｎ−プロピル−Ｎ−
〔２−（４−メチルフェノキシ）−１−メチルエチル〕
アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−ｎ−プロピル−Ｎ−
〔２−（４−メトキシフェノキシ）−１−メチルエチ
ル〕アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−ｎ−プロピル−Ｎ−
（３−フェノキシプロピル）アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−ｎ−プロピル−Ｎ−
（６−フェノキシヘキシル）アミノエチルエステル ４−ヒドロキシ安息香酸 ３−Ｎ−ｎ−プロピル−Ｎ−
（２−フェノキシエチル）アミノプロピルエステル ４−ヒドロキシ安息香酸 ６−Ｎ−ｎ−プロピル−Ｎ−
（２−フェノキシエチル）アミノヘキシルエステル ４−ヒドロキシ安息香酸 ９−Ｎ−ｎ−プロピル−Ｎ−
（２−フェノキシエチル）アミノノニルエステル4-Hydroxybenzoic acid 2-Nn-propyl-N- (2-phenoxyethyl) aminoethyl ester 4-Hydroxybenzoic acid 2-Nn-propyl-N-
[2- (4-chlorophenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-Nn-propyl-N-
[2- (4-Methylphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-Nn-propyl-N-
[2- (4-Methoxyphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-Nn-propyl-N-
(2-phenoxy-1-methylethyl) aminoethyl ester 4-hydroxybenzoic acid 2-Nn-propyl-N-
[2- (4-chlorophenoxy) -1-methylethyl]
Aminoethyl ester 4-hydroxybenzoic acid 2-Nn-propyl-N-
[2- (4-methylphenoxy) -1-methylethyl]
Aminoethyl ester 4-hydroxybenzoic acid 2-Nn-propyl-N-
[2- (4-Methoxyphenoxy) -1-methylethyl] aminoethyl ester 4-hydroxybenzoic acid 2-Nn-propyl-N-
(3-phenoxypropyl) aminoethyl ester 4-hydroxybenzoic acid 2-Nn-propyl-N-
(6-Phenoxyhexyl) aminoethyl ester 4-hydroxybenzoic acid 3-Nn-propyl-N-
(2-phenoxyethyl) aminopropyl ester 4-hydroxybenzoic acid 6-Nn-propyl-N-
(2-phenoxyethyl) aminohexyl ester 4-hydroxybenzoic acid 9-Nn-propyl-N-
(2-phenoxyethyl) aminononyl ester
【００２２】４−ヒドロキシ安息香酸 ２−Ｎ−iso-プ
ロピル−Ｎ−（２−フェノキシエチル）アミノエチルエ
ステル ４−ヒドロキシ安息香酸 ２−Ｎ−iso-プロピル−Ｎ−
〔２−（４−クロロフェノキシ）エチル〕アミノエチル
エステル ４−ヒドロキシ安息香酸 ２−Ｎ−iso-プロピル−Ｎ−
〔２−（４−メチルフェノキシ）エチル〕アミノエチル
エステル ４−ヒドロキシ安息香酸 ２−Ｎ−iso-プロピル−Ｎ−
〔２−（４−メトキシフェノキシ）エチル〕アミノエチ
ルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−iso-プロピル−Ｎ−
（２−フェノキシ−１−メチルエチル）アミノエチルエ
ステル ４−ヒドロキシ安息香酸 ２−Ｎ−iso-プロピル−Ｎ−
〔２−（４−クロロフェノキシ）−１−メチルエチル〕
アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−iso-プロピル−Ｎ−
〔２−（４−メチルフェノキシ）−１−メチルエチル〕
アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−iso-プロピル−Ｎ−
〔２−（４−メトキシフェノキシ）−１−メチルエチ
ル〕アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−iso-プロピル−Ｎ−
（３−フェノキシプロピル）アミノエチルエステル ４−ヒドロキシ安息香酸 ２−Ｎ−iso-プロピル−Ｎ−
（６−フェノキシヘキシル）アミノエチルエステル ４−ヒドロキシ安息香酸 ３−Ｎ−iso-プロピル−Ｎ−
（２−フェノキシエチル）アミノプロピルエステル ４−ヒドロキシ安息香酸 ６−Ｎ−iso-プロピル−Ｎ−
（２−フェノキシエチル）アミノヘキシルエステル ４−ヒドロキシ安息香酸 ９−Ｎ−iso-プロピル−Ｎ−
（２−フェノキシエチル）アミノノニルエステル4-Hydroxybenzoic acid 2-N-iso-propyl-N- (2-phenoxyethyl) aminoethyl ester 4-Hydroxybenzoic acid 2-N-iso-propyl-N-
[2- (4-chlorophenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-iso-propyl-N-
[2- (4-Methylphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-iso-propyl-N-
[2- (4-Methoxyphenoxy) ethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-iso-propyl-N-
(2-phenoxy-1-methylethyl) aminoethyl ester 4-hydroxybenzoic acid 2-N-iso-propyl-N-
[2- (4-chlorophenoxy) -1-methylethyl]
Aminoethyl ester 4-hydroxybenzoic acid 2-N-iso-propyl-N-
[2- (4-methylphenoxy) -1-methylethyl]
Aminoethyl ester 4-hydroxybenzoic acid 2-N-iso-propyl-N-
[2- (4-Methoxyphenoxy) -1-methylethyl] aminoethyl ester 4-hydroxybenzoic acid 2-N-iso-propyl-N-
(3-phenoxypropyl) aminoethyl ester 4-hydroxybenzoic acid 2-N-iso-propyl-N-
(6-Phenoxyhexyl) aminoethyl ester 4-hydroxybenzoic acid 3-N-iso-propyl-N-
(2-phenoxyethyl) aminopropyl ester 4-hydroxybenzoic acid 6-N-iso-propyl-N-
(2-phenoxyethyl) aminohexyl ester 4-hydroxybenzoic acid 9-N-iso-propyl-N-
(2-phenoxyethyl) aminononyl ester
【００２３】一般式（Ｉ）で表される本発明の化合物
は、４−ヒドロキシ安息香酸の水酸基をベンジル基もし
くはアセチル基等で保護した後に酸クロライドとし、対
応する置換アミノアルコールとエステル化した後、水酸
基の保護基を脱保護することによって得られる。このと
きの酸クロライド化剤としては塩化チオニル、オキシ塩
化リン、五塩化リン、蓚酸ジクロライド等が挙げられ、
対応する安息香酸に対して１〜１０倍当量用いる。反応
はアセトニトリル、ベンゼン、トルエン等の溶媒を用い
るか、もしくは無溶媒で行なう。反応温度は−１０〜１
５０℃で行ない、好ましくは０〜１２０℃で行なう。こ
のとき反応促進剤としてピリジン、ジメチルホルムアミ
ド等を触媒量添加してもよい。エステル化に際しては、
塩基としてトリエチルアミン、ピリジン等を酸クロライ
ドの１〜５倍当量用いて行なう。置換アミノアルコール
は酸クロライドに対して１〜３倍当量用いる。反応溶媒
としてはアセトニトリル、ベンゼン、トルエン、塩化メ
チレン、クロロホルム、テトラヒドロフラン、酢酸エチ
ル等が挙げられ、酸クロライドに対して１〜１００倍当
量用いる。脱保護については、保護基がベンジル基の場
合にはパラジウムカーボン等を用いた接触水素還元によ
り、また保護基がアセチル基の場合にはメタノール、エ
タノールの存在下、酢酸ナトリウム、炭酸カリウム、炭
酸ナトリウム等を０〜６０℃で作用させることにより行
なうことができる。The compound of the present invention represented by the general formula (I) is prepared by protecting the hydroxyl group of 4-hydroxybenzoic acid with a benzyl group, an acetyl group or the like to form an acid chloride, and then esterifying with a corresponding substituted amino alcohol. It is obtained by deprotecting the hydroxyl-protecting group. Examples of the acid chloride agent at this time include thionyl chloride, phosphorus oxychloride, phosphorus pentachloride, oxalic acid dichloride, and the like.
Use 1 to 10 equivalents relative to the corresponding benzoic acid. The reaction is carried out using a solvent such as acetonitrile, benzene, toluene or the like or without a solvent. Reaction temperature is -10 to 1
It is carried out at 50 ° C, preferably 0 to 120 ° C. At this time, pyridine, dimethylformamide or the like may be added as a reaction promoter in a catalytic amount. When esterifying,
Triethylamine, pyridine or the like is used as a base in an amount of 1 to 5 times equivalent to that of acid chloride. The substituted amino alcohol is used in 1 to 3 equivalents based on the acid chloride. Examples of the reaction solvent include acetonitrile, benzene, toluene, methylene chloride, chloroform, tetrahydrofuran, ethyl acetate, etc., and are used in an amount of 1 to 100 equivalents based on the acid chloride. For deprotection, when the protecting group is a benzyl group, catalytic hydrogen reduction using palladium carbon or the like, and when the protecting group is an acetyl group, sodium acetate, potassium carbonate, sodium carbonate in the presence of methanol or ethanol is used. And the like at 0-60 ° C.
【００２４】また、適当な縮合剤の存在下、ヒドロキシ
安息香酸もしくはその低級アルキルエステル等と対応す
る置換アミノアルコールとを脱水縮合又はエステル交換
させることにより容易に得ることができる。置換アミノ
アルコールはヒドロキシ安息香酸もしくはその低級アル
キルエステルに対して１〜３倍当量用いる。このときの
縮合剤又は触媒としては、硫酸、ポリリン酸、パラトル
エンスルホン酸、アンバーリスト等の脱水剤又はエステ
ル交換触媒が挙げられる。これらの脱水剤は置換アミノ
アルコールに対して１．０１〜１０倍当量用いて行な
う。溶媒としては、ベンゼン、トルエン、キシレン、メ
シチレンもしくは反応試剤の置換アミノアルコールを用
いて行なう。さらには、４−ヒドロキシ安息香酸 ハロ
ゲノアルキルエステルと対応する２級アミンとを反応さ
せることによっても得ることができる。このときの塩基
としては炭酸水素ナトリウム、炭酸水素カリウム、炭酸
ナトリウム、炭酸カリウム等の弱塩基を用いる。反応溶
媒としては、メタノール、エタノール、プロパノール、
ジメチルホルムアミド、ジメチルアセトアミド、Ｎ−メ
チルピロリドン、スルホラン等を用いて行なう。反応温
度は５０〜１５０℃で行なう。以下、本発明を実施例に
よって詳述するが本発明はこれらの実施例によって制限
されるものではない。Further, it can be easily obtained by dehydration condensation or transesterification of hydroxybenzoic acid or its lower alkyl ester and the corresponding substituted amino alcohol in the presence of a suitable condensing agent. The substituted amino alcohol is used in 1 to 3 equivalents relative to hydroxybenzoic acid or its lower alkyl ester. Examples of the condensing agent or catalyst at this time include a dehydrating agent such as sulfuric acid, polyphosphoric acid, paratoluenesulfonic acid, and amberlyst, or a transesterification catalyst. These dehydrating agents are used in an amount of 1.01 to 10 times equivalent to the substituted amino alcohol. As the solvent, benzene, toluene, xylene, mesitylene, or a substituted amino alcohol as a reaction reagent is used. Furthermore, it can also be obtained by reacting a 4-hydroxybenzoic acid halogenoalkyl ester with a corresponding secondary amine. As the base at this time, a weak base such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate or potassium carbonate is used. As the reaction solvent, methanol, ethanol, propanol,
It is carried out using dimethylformamide, dimethylacetamide, N-methylpyrrolidone, sulfolane and the like. The reaction temperature is 50 to 150 ° C. Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited to these Examples.
【００２５】[0025]
〔実施例１〕４−ヒドロキシ安息香酸 ２−Ｎ−メチル
−Ｎ−（２−フェノキシエチル）アミノエチルエステル
の合成[Example 1] Synthesis of 4-hydroxybenzoic acid 2-N-methyl-N- (2-phenoxyethyl) aminoethyl ester
【００２６】[0026]
【化７】 [Chemical 7]
【００２７】４−ベンジルオキシ安息香酸９ｇに塩化チ
オニル５ｇ、トルエン１５０ｍｌを加え、さらにジメチ
ルホルムアミド数滴を加え８０℃で３時間攪拌後、溶媒
を減圧留去し９．７ｇの４−ベンジルオキシ安息香酸ク
ロライドを固体として得た。２−Ｎ−メチル−Ｎ−（２
−フェノキシエチル）アミノエタノール７．８ｇ、トリ
エチルアミン２０ｍｌのトルエン溶液５０ｍｌに４−ベ
ンジルオキシ安息香酸クロライド９．７ｇのトルエン溶
液１００ｍｌを攪拌下に加え室温で３０分攪拌後、水を
加え有機層を水洗後、溶媒留去した。残渣をシリカゲル
カラムクロマトグラフィー（流出溶媒：ヘキサン／酢酸
エチル＝３／１）で精製し４−ベンジルオキシ安息香酸
２−Ｎ−メチル−Ｎ−（２−フェノキシエチル）アミ
ノエチルエステル１２ｇを得た。これに触媒として１０
％パラジウムカーボン１ｇ、エタノール５０ｍｌ、酢酸
エチル５０ｍｌを加え水素雰囲気下、常温、常圧で３時
間攪拌した。触媒を炉別後、溶媒留去しヘキサン／酢酸
エチル混合溶媒から再結晶して目的とする４−ヒドロキ
シ安息香酸 ２−Ｎ−メチル−Ｎ−（２−フェノキシエ
チル）アミノエチルエステル６．７ｇを得た。 融点 １２１〜１２２℃1 Ｈ−ＮＭＲ（ＣＤＣｌ3 ）：δ 2.50(s,3H), 2.96〜
3.02(m,4H), 4.12(t,2H), 4.45(t,2H), 6.68(d,2H), 6.
88(d,2H), 6.92(t,1H), 7.26(t,2H), 7.78(d,2H)To 9 g of 4-benzyloxybenzoic acid, 5 g of thionyl chloride and 150 ml of toluene were added, and several drops of dimethylformamide were added, and the mixture was stirred at 80 ° C. for 3 hours, and the solvent was distilled off under reduced pressure to give 9.7 g of 4-benzyloxybenzoic acid. The acid chloride was obtained as a solid. 2-N-methyl-N- (2
-Phenoxyethyl) aminoethanol 7.8 g, triethylamine 20 ml in a toluene solution 50 ml, 4-benzyloxybenzoic acid chloride 9.7 g in a toluene solution 100 ml with stirring and after stirring at room temperature for 30 minutes, water was added to wash the organic layer with water. After that, the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 3/1) to obtain 12 g of 4-benzyloxybenzoic acid 2-N-methyl-N- (2-phenoxyethyl) aminoethyl ester. 10 as a catalyst for this
% Palladium carbon 1 g, ethanol 50 ml, and ethyl acetate 50 ml were added, and the mixture was stirred under a hydrogen atmosphere at room temperature and atmospheric pressure for 3 hours. After separating the catalyst from the furnace, the solvent was distilled off and recrystallized from a mixed solvent of hexane / ethyl acetate to give 6.7 g of the target 4-hydroxybenzoic acid 2-N-methyl-N- (2-phenoxyethyl) aminoethyl ester. Obtained. Melting point 121-122 ° C 1 H-NMR (CDCl 3 ): δ 2.50 (s, 3H), 2.96-
3.02 (m, 4H), 4.12 (t, 2H), 4.45 (t, 2H), 6.68 (d, 2H), 6.
88 (d, 2H), 6.92 (t, 1H), 7.26 (t, 2H), 7.78 (d, 2H)
【００２８】〔実施例２〕４−ヒドロキシ安息香酸 ２
−Ｎ−メチル−Ｎ−（２−フェノキシ−１−メチルエチ
ル）アミノエチルエステルの合成Example 2 4-Hydroxybenzoic acid 2
Synthesis of -N-methyl-N- (2-phenoxy-1-methylethyl) aminoethyl ester
【００２９】[0029]
【化８】 Embedded image
【００３０】４−アセチルオキシ安息香酸７．１ｇに塩
化チオニル５ｇ、トルエン１０ｍｌを加え、さらにジメ
チルホルムアミド数滴を加え８０℃で３時間攪拌後、溶
媒を減圧留去し７．９ｇの４−アセチルオキシ安息香酸
クロライドを得た。２−Ｎ−メチル−Ｎ−（２−フェノ
キシ−１−メチルエチル）アミノエタノール８．４ｇ、
トリエチルアミン１０ｍｌの酢酸エチル溶液３０ｍｌに
４−アセチルオキシ安息香酸クロライド７．９ｇの酢酸
エチル溶液５０ｍｌを攪拌下に加え室温で１時間攪拌し
た。この反応液を濾過し、濾液から溶媒を留去後、炭酸
カリウム３ｇ、メタノール５０ｍｌを加え２時間攪拌し
た。反応液を濾過し、濾液から溶媒を留去後、残渣をシ
リカゲルカラムクロマトグラフィー（流出溶媒：ヘキサ
ン／酢酸エチル＝１／１）で精製し、ヘキサン／酢酸エ
チル混合溶媒から再結晶して目的とする４−ヒドロキシ
安息香酸 ２−Ｎ−メチル−Ｎ−（２−フェノキシ−１
−メチルエチル）アミノエチルエステル５．４ｇを得
た。 融点 ９７〜９９℃1 Ｈ−ＮＭＲ（ＣＤＣｌ3 ）：δ 1.18(d,3H), 2.45(s,
3H), 2.92〜2.98(m,2H), 3.19〜3.26(m,1H), 3.82〜3.8
9(m,1H), 4.04〜4.09(m,1H), 4.39(t,2H), 6.74(d,2H),
6.89(d,2H), 6.92(t,1H), 7.25(t,2H), 7.83(d,2H)To 7.1 g of 4-acetyloxybenzoic acid, 5 g of thionyl chloride and 10 ml of toluene were added, and several drops of dimethylformamide were added. After stirring at 80 ° C. for 3 hours, the solvent was distilled off under reduced pressure to give 7.9 g of 4-acetyl. Oxybenzoic acid chloride was obtained. 2-N-methyl-N- (2-phenoxy-1-methylethyl) aminoethanol 8.4 g,
To 30 ml of an ethyl acetate solution containing 10 ml of triethylamine, 50 ml of an ethyl acetate solution containing 7.9 g of 4-acetyloxybenzoic acid chloride was added with stirring, and the mixture was stirred at room temperature for 1 hour. The reaction solution was filtered, the solvent was distilled off from the filtrate, 3 g of potassium carbonate and 50 ml of methanol were added, and the mixture was stirred for 2 hours. The reaction solution is filtered, the solvent is distilled off from the filtrate, the residue is purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 1/1), and recrystallized from a hexane / ethyl acetate mixed solvent to give the desired compound. 4-hydroxybenzoic acid 2-N-methyl-N- (2-phenoxy-1
-Methylethyl) aminoethyl ester 5.4 g was obtained. Melting point 97-99 ° C 1 H-NMR (CDCl 3 ): δ 1.18 (d, 3H), 2.45 (s,
3H), 2.92 ~ 2.98 (m, 2H), 3.19 ~ 3.26 (m, 1H), 3.82 ~ 3.8
9 (m, 1H), 4.04 to 4.09 (m, 1H), 4.39 (t, 2H), 6.74 (d, 2H),
6.89 (d, 2H), 6.92 (t, 1H), 7.25 (t, 2H), 7.83 (d, 2H)
【００３１】〔実施例３〕４−ヒドロキシ安息香酸 ２
−Ｎ−エチル−Ｎ−（２−フェノキシエチル）アミノエ
チルエステルの合成[Example 3] 4-hydroxybenzoic acid 2
Synthesis of -N-ethyl-N- (2-phenoxyethyl) aminoethyl ester
【００３２】[0032]
【化９】 Embedded image
【００３３】４−ヒドロキシ安息香酸１４ｇ、２−Ｎ−
エチル−Ｎ−（２−フェノキシエチル）アミノエタノー
ル２１ｇ、ｐ−トルエンスルホン酸一水和物２３ｇにト
ルエン２００ｍｌを加え、１７時間共沸脱水を行なっ
た。室温まで冷却してから重曹水、次いで水で有機層を
洗浄し、溶媒留去後、残渣をシリカゲルカラムクロマト
グラフィー（流出溶媒：ヘキサン／酢酸エチル＝１／
１）で精製し、ヘキサン／酢酸エチル混合溶媒から再結
晶して目的とする４−ヒドロキシ安息香酸 ２−Ｎ−エ
チル−Ｎ−（２−フェノキシエチル）アミノエチルエス
テル３ｇを得た。 融点 ７２〜７３℃1 Ｈ−ＮＭＲ（ＣＤＣｌ3 ）：δ 1.11(t,3H), 2.79(q,
2H), 3.01〜3.06(m,4H), 4.10(t,2H), 4.42(t,2H), 6.7
4(d,2H), 6.87(d,2H), 6.91(t,1H), 7.24(t,2H), 7.82
(d,2H)4-Hydroxybenzoic acid 14 g, 2-N-
To 21 g of ethyl-N- (2-phenoxyethyl) aminoethanol and 23 g of p-toluenesulfonic acid monohydrate, 200 ml of toluene was added, and azeotropic dehydration was performed for 17 hours. After cooling to room temperature, the organic layer was washed with aqueous sodium hydrogen carbonate and then with water, and the solvent was distilled off. The residue was subjected to silica gel column chromatography (eluent: hexane / ethyl acetate = 1 /
The product was purified in 1) and recrystallized from a mixed solvent of hexane / ethyl acetate to obtain 3 g of a target 4-hydroxybenzoic acid 2-N-ethyl-N- (2-phenoxyethyl) aminoethyl ester. Melting point 72-73 ° C. 1 H-NMR (CDCl 3 ): δ 1.11 (t, 3H), 2.79 (q,
2H), 3.01 to 3.06 (m, 4H), 4.10 (t, 2H), 4.42 (t, 2H), 6.7
4 (d, 2H), 6.87 (d, 2H), 6.91 (t, 1H), 7.24 (t, 2H), 7.82
(d, 2H)
【００３４】〔応用例１〕カプラー（Ａ−１）の2x10-2
Ｍ酢酸エチル溶液１ｍｌと実施例１の４−ヒドロキシ安
息香酸 ２−Ｎ−メチル−Ｎ−（２−フェノキシエチ
ル）アミノエチルエステルの2x10-2Ｍ酢酸エチル溶液１
ｍｌの混合溶液を、ジアゾ化合物（Ａ−２）の1x10-4Ｍ
酢酸エチル溶液２ｍｌに２５℃で加えた時のカップリン
グ速度定数を４８０nmでの吸光度変化から求めたとこ
ろ、２．１ｘ１０-3(sec-1) であった。[Application Example 1] 2x10 -2 of coupler (A-1)
1 ml of M ethyl acetate solution and 2 × 10 −2 M ethyl acetate solution of 4-hydroxybenzoic acid 2-N-methyl-N- (2-phenoxyethyl) aminoethyl ester of Example 1
ml of the mixed solution was added to the diazo compound (A-2) at 1 × 10 −4 M
The coupling rate constant when added to 2 ml of an ethyl acetate solution at 25 ° C. was 2.1 × 10 −3 (sec −1 ) as determined from the change in absorbance at 480 nm.
【００３５】[0035]
【化１０】 Embedded image
【００３６】それに対して４−ヒドロキシ安息香酸 ２
−Ｎ−メチル−Ｎ−（２−フェノキシエチル）アミノエ
チルエステルに代えて安息香酸 ２−Ｎ−メチル−Ｎ−
（２−フェノキシエチル）アミノエチルエステルを用い
た他は同様の条件にてカップリング速度定数を求めたと
ころ、０．８ｘ１０-3(sec-1) であった。以上の結果よ
り本発明の置換アミノ基含有安息香酸エステル誘導体は
ジアゾ化合物のカップリング反応の反応性向上に有効で
あることが明らかである。On the other hand, 4-hydroxybenzoic acid 2
Benzoic acid 2-N-methyl-N-in place of -N-methyl-N- (2-phenoxyethyl) aminoethyl ester
When the coupling rate constant was determined under the same conditions except that (2-phenoxyethyl) aminoethyl ester was used, it was 0.8 × 10 −3 (sec −1 ). From the above results, it is clear that the substituted amino group-containing benzoic acid ester derivative of the present invention is effective for improving the reactivity of the coupling reaction of the diazo compound.
Claims (1)
息香酸エステル誘導体。 一般式（Ｉ） 【化１】 式中、Ｒ1 は炭素数１〜６の直鎖もしくは分岐のアルキ
ル基を示し、Ａｒはアリール基を示し、ｍは２〜６の整
数を示し、ｎは２〜９の整数を示し、Ｘは水素原子、ハ
ロゲン原子、水酸基、低級アルキル基、低級アルコキシ
基を示す。1. An amino group-containing benzoic acid ester derivative represented by the general formula (I). General formula (I) In the formula, R 1 represents a linear or branched alkyl group having 1 to 6 carbon atoms, Ar represents an aryl group, m represents an integer of 2 to 6, n represents an integer of 2 to 9, and X represents Represents a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group, and a lower alkoxy group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7228730A JPH0971557A (en) | 1995-09-06 | 1995-09-06 | Amino group-containing benzoic ester derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7228730A JPH0971557A (en) | 1995-09-06 | 1995-09-06 | Amino group-containing benzoic ester derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0971557A true JPH0971557A (en) | 1997-03-18 |
Family
ID=16880919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7228730A Pending JPH0971557A (en) | 1995-09-06 | 1995-09-06 | Amino group-containing benzoic ester derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0971557A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011510070A (en) * | 2008-01-22 | 2011-03-31 | ユニヴェルシテット・ヤジェロンスキ | Derivatives of aminoalkanols, methods for obtaining aminoalkanols and their use |
-
1995
- 1995-09-06 JP JP7228730A patent/JPH0971557A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011510070A (en) * | 2008-01-22 | 2011-03-31 | ユニヴェルシテット・ヤジェロンスキ | Derivatives of aminoalkanols, methods for obtaining aminoalkanols and their use |
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