TWI320782B - - Google Patents

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Publication number: TWI320782B
Authority: TW; Taiwan
Prior art keywords: group; formula; compound; reaction; alkyl
Prior art date: 2002-07-11

Application number

TW92119053A

Other languages

English (en)

Chinese (zh)

Other versions

TW200401767A (en

Inventor

Hiroshi Kurihara

Kazumi Yamamoto

Original Assignee

Meiji Seika Kaisha

Priority date (The priority date 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 date listed.)

2002-07-11

Filing date

2003-07-11

Publication date

2010-02-21

2003-07-11 Application filed by Meiji Seika Kaisha filed Critical Meiji Seika Kaisha

2004-02-01 Publication of TW200401767A publication Critical patent/TW200401767A/zh

2010-02-21 Application granted granted Critical

2010-02-21 Publication of TWI320782B publication Critical patent/TWI320782B/zh

Links

125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 22
238000007363 ring formation reaction Methods 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
238000000034 method Methods 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
239000011592 zinc chloride Substances 0.000 claims description 4
235000005074 zinc chloride Nutrition 0.000 claims description 4
CFHAYNINGQHXOI-UHFFFAOYSA-N acetic acid ethyl propanoate Chemical compound CC(O)=O.CCOC(=O)CC CFHAYNINGQHXOI-UHFFFAOYSA-N 0.000 claims description 2
150000001336 alkenes Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
125000001424 substituent group Chemical group 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
MQMRDVGCUXIFHE-UHFFFAOYSA-N C1=CC=C2C(=C1)C=C(N2)C3=CC(=C(C=C3)N)F Chemical class C1=CC=C2C(=C1)C=C(N2)C3=CC(=C(C=C3)N)F MQMRDVGCUXIFHE-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
230000029936 alkylation Effects 0.000 claims 1
238000005804 alkylation reaction Methods 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 20
238000003756 stirring Methods 0.000 description 18
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 14
239000012044 organic layer Substances 0.000 description 13
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
238000010438 heat treatment Methods 0.000 description 11
101150041968 CDC13 gene Proteins 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229940093499 ethyl acetate Drugs 0.000 description 9
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
150000002081 enamines Chemical class 0.000 description 7
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000011521 glass Substances 0.000 description 6
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
238000000926 separation method Methods 0.000 description 6
239000007787 solid Substances 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
125000003277 amino group Chemical group 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
-1 enamine compound Chemical class 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000004448 alkyl carbonyl group Chemical group 0.000 description 3
238000005576 amination reaction Methods 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000002451 electron ionisation mass spectrometry Methods 0.000 description 3
239000000499 gel Substances 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
LFIQWXFTKOLHPM-UHFFFAOYSA-N 4-cyclohexyl-2-fluoroaniline Chemical compound C1=C(F)C(N)=CC=C1C1CCCCC1 LFIQWXFTKOLHPM-UHFFFAOYSA-N 0.000 description 2
BKDLIDXUWLWPSD-UHFFFAOYSA-N 4-tert-butyl-2-fluoroaniline Chemical compound CC(C)(C)C1=CC=C(N)C(F)=C1 BKDLIDXUWLWPSD-UHFFFAOYSA-N 0.000 description 2
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical group CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000012295 chemical reaction liquid Substances 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical compound FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-UHFFFAOYSA-N 0.000 description 1
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
UYTJAHDDQVFRBS-UHFFFAOYSA-N 1-fluoro-2-nitrosobenzene Chemical compound FC1=CC=CC=C1N=O UYTJAHDDQVFRBS-UHFFFAOYSA-N 0.000 description 1
TZDZZIWEBDGFBS-UHFFFAOYSA-N 8-fluoro-2,3-dimethyl-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)C(C)=C(C)NC2=C1F TZDZZIWEBDGFBS-UHFFFAOYSA-N 0.000 description 1
206010067484 Adverse reaction Diseases 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
JAGZUIGGHGTFHO-UHFFFAOYSA-N Ethyl 3-phenylpropanoate Chemical compound CCOC(=O)CCC1=CC=CC=C1 JAGZUIGGHGTFHO-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000006838 adverse reaction Effects 0.000 description 1
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000006837 decompression Effects 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
UDOUIRSXTJAWOV-UHFFFAOYSA-N ethyl acetate;propyl acetate Chemical compound CCOC(C)=O.CCCOC(C)=O UDOUIRSXTJAWOV-UHFFFAOYSA-N 0.000 description 1
OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 description 1
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
GGPGYOXIQRDAJC-UHFFFAOYSA-N n,n',n'-trimethylacetohydrazide Chemical compound CN(C)N(C)C(C)=O GGPGYOXIQRDAJC-UHFFFAOYSA-N 0.000 description 1
WEMUHCTTYPBGCT-UHFFFAOYSA-N n-butyl-2-fluoroaniline Chemical compound CCCCNC1=CC=CC=C1F WEMUHCTTYPBGCT-UHFFFAOYSA-N 0.000 description 1
MGNPLIACIXIYJE-UHFFFAOYSA-N n-fluoroaniline Chemical compound FNC1=CC=CC=C1 MGNPLIACIXIYJE-UHFFFAOYSA-N 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
230000006911 nucleation Effects 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
150000004032 porphyrins Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000004059 quinone derivatives Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007670 refining Methods 0.000 description 1
238000005070 sampling Methods 0.000 description 1
235000018553 tannin Nutrition 0.000 description 1
229920001864 tannin Polymers 0.000 description 1
239000001648 tannin Substances 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

TW92119053A 2002-07-11 2003-07-11 Process for producing 2, 3, 6-trialkyl-8-fluoro-4-quinoline derivatives TW200401767A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2002202213		2002-07-11

Publications (2)

Publication Number	Publication Date
TW200401767A TW200401767A (en)	2004-02-01
TWI320782B true TWI320782B (de)	2010-02-21

Family

ID=30112610

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW92119053A TW200401767A (en)	2002-07-11	2003-07-11	Process for producing 2, 3, 6-trialkyl-8-fluoro-4-quinoline derivatives

Country Status (5)

Country	Link
JP (1)	JP4541143B2 (de)
CN (1)	CN1307160C (de)
AU (1)	AU2003280976A1 (de)
TW (1)	TW200401767A (de)
WO (1)	WO2004007460A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5558352B2 (ja) *	2008-07-15	2014-07-23	日本化薬株式会社	６−アリールオキシキノリン誘導体の製造方法およびその中間体
CN104904720B (zh) *	2014-03-11	2017-08-08	浙江省化工研究院有限公司	一种含zj5337和甲氧基丙烯酸酯类杀菌剂的杀菌组合物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5828865B2 (ja) *	1978-06-21	1983-06-18	保土谷化学工業株式会社	２↓−クロロ↓−４′↓−ヒドロキシ↓−ジフエニルアミンの改良製造法
US4436936A (en) *	1981-06-19	1984-03-13	Ciba-Geigy Corporation	Alkylation and aralkylation of aromatic amines
EP0079093B1 (de) *	1981-11-11	1986-06-11	Shell Internationale Researchmaatschappij B.V.	Verfahren zur selektiven Alkylierung eines Anilins
JPS59167545A (ja) *	1983-02-01	1984-09-21	Nippon Kayaku Co Ltd	３−メチル−４−イソプロピルアニリンの製造方法
TW521072B (en) *	1997-06-02	2003-02-21	Meiji Seika Kaisha	4-quinolinol derivatives and fungicides containing the same as an active ingredient used for agriculture and horticulture
KR100720776B1 (ko) *	2000-05-30	2007-05-22	메이지 세이카 가부시키가이샤	벼도열병 방제제

2003
- 2003-07-11 AU AU2003280976A patent/AU2003280976A1/en not_active Abandoned
- 2003-07-11 JP JP2004521196A patent/JP4541143B2/ja not_active Expired - Fee Related
- 2003-07-11 TW TW92119053A patent/TW200401767A/zh not_active IP Right Cessation
- 2003-07-11 WO PCT/JP2003/008848 patent/WO2004007460A1/ja not_active Ceased
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AU2003280976A1 (en)	2004-02-02
CN1668597A (zh)	2005-09-14
TW200401767A (en)	2004-02-01
JP4541143B2 (ja)	2010-09-08
JPWO2004007460A1 (ja)	2005-11-10
WO2004007460A1 (ja)	2004-01-22
CN1307160C (zh)	2007-03-28

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