CA1177086A - Methode de substitution nucleophile - Google Patents

Methode de substitution nucleophile

Info

Publication number: CA1177086A
Authority: CA; Canada
Prior art keywords: alpha; propionitrile; nitrophenyl; propionic acid; fluoro
Prior art date: 1981-11-02
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.): Expired

Application number

CA000414303A

Other languages

English (en)

Inventor

Barbara C. Stahly

G. Patrick Stahly

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ethyl Corp

Original Assignee

Ethyl Corp

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.)

1981-11-02

Filing date

1982-10-27

Publication date

1984-10-30

1981-11-02 Priority claimed from US06/317,321 external-priority patent/US4370278A/en

1982-10-27 Application filed by Ethyl Corp filed Critical Ethyl Corp

1984-10-30 Application granted granted Critical

1984-10-30 Publication of CA1177086A publication Critical patent/CA1177086A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 41
238000010534 nucleophilic substitution reaction Methods 0.000 title abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 38
150000002825 nitriles Chemical class 0.000 claims abstract description 24
-1 alpha,alpha-disubstituted acetonitrile Chemical class 0.000 claims abstract description 16
239000000010 aprotic solvent Substances 0.000 claims abstract description 8
229910052799 carbon Inorganic materials 0.000 claims abstract description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 27
239000002585 base Substances 0.000 claims description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 16
229910000104 sodium hydride Inorganic materials 0.000 claims description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 11
239000012312 sodium hydride Substances 0.000 claims description 11
QCPKTMACPAKCKW-UHFFFAOYSA-N 2-(4-nitrophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C([N+]([O-])=O)C=C1 QCPKTMACPAKCKW-UHFFFAOYSA-N 0.000 claims description 9
PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 claims description 7
PYNYHMRMZOGVML-UHFFFAOYSA-N 2-bromopropanenitrile Chemical compound CC(Br)C#N PYNYHMRMZOGVML-UHFFFAOYSA-N 0.000 claims description 7
OJBIYTLSPCCEJZ-UHFFFAOYSA-N 2-(3-fluoro-4-nitrophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C([N+]([O-])=O)C(F)=C1 OJBIYTLSPCCEJZ-UHFFFAOYSA-N 0.000 claims description 6
RZSVLKAIDMAXLB-UHFFFAOYSA-N 2-(4-aminophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C(N)C=C1 RZSVLKAIDMAXLB-UHFFFAOYSA-N 0.000 claims description 6
150000001339 alkali metal compounds Chemical class 0.000 claims description 6
KQKTZBAKYYSFFJ-UHFFFAOYSA-N 2-[4-(1,3-dioxoisoindol-2-yl)phenyl]propanenitrile Chemical compound C1=CC(C(C#N)C)=CC=C1N1C(=O)C2=CC=CC=C2C1=O KQKTZBAKYYSFFJ-UHFFFAOYSA-N 0.000 claims description 5
ACRMAHMDLNNSNK-UHFFFAOYSA-N 2-[4-(1,3-dioxoisoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1=O ACRMAHMDLNNSNK-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 5
SXROZCCZEGDMNU-UHFFFAOYSA-N 2-(4-amino-3-fluorophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C(N)C(F)=C1 SXROZCCZEGDMNU-UHFFFAOYSA-N 0.000 claims description 4
WOMVICAMAQURRN-UHFFFAOYSA-N 2-(4-aminophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(N)C=C1 WOMVICAMAQURRN-UHFFFAOYSA-N 0.000 claims description 4
150000007960 acetonitrile Chemical class 0.000 claims description 4
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 4
229910000105 potassium hydride Inorganic materials 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
238000006467 substitution reaction Methods 0.000 claims description 4
OAVUAKGAEPSSLW-UHFFFAOYSA-N 2-(3-fluoro-4-phenylphenyl)propanenitrile Chemical compound FC1=CC(C(C#N)C)=CC=C1C1=CC=CC=C1 OAVUAKGAEPSSLW-UHFFFAOYSA-N 0.000 claims description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims 4
RBSRRICSXWXMRC-UHFFFAOYSA-N 2-(4-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C([N+]([O-])=O)C=C1 RBSRRICSXWXMRC-UHFFFAOYSA-N 0.000 claims 2
RJMIEHBSYVWVIN-UHFFFAOYSA-N indoprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-UHFFFAOYSA-N 0.000 claims 2
LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 claims 2
PXNJGLAVKOXITN-UHFFFAOYSA-N 2-(4-nitrophenyl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=C(CC#N)C=C1 PXNJGLAVKOXITN-UHFFFAOYSA-N 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 16
239000000047 product Substances 0.000 description 13
239000003921 oil Substances 0.000 description 11
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 10
239000001257 hydrogen Substances 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
239000000376 reactant Substances 0.000 description 8
JNAYPRPPXRWGQO-UHFFFAOYSA-N 2-chloropropanenitrile Chemical compound CC(Cl)C#N JNAYPRPPXRWGQO-UHFFFAOYSA-N 0.000 description 7
239000010410 layer Substances 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 6
239000002480 mineral oil Substances 0.000 description 6
235000010446 mineral oil Nutrition 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
125000001246 bromo group Chemical group Br* 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
229910000102 alkali metal hydride Inorganic materials 0.000 description 4
150000008046 alkali metal hydrides Chemical class 0.000 description 4
229960004187 indoprofen Drugs 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
125000002346 iodo group Chemical group I* 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
239000002002 slurry Substances 0.000 description 4
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000005181 nitrobenzenes Chemical class 0.000 description 3
239000007858 starting material Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
MRCKRGSNLOHYRA-UHFFFAOYSA-N (2-nitrophenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1[N+]([O-])=O MRCKRGSNLOHYRA-UHFFFAOYSA-N 0.000 description 2
WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 2
CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical class [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
150000001491 aromatic compounds Chemical class 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
150000003983 crown ethers Chemical class 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
AYDXAULLCROVIT-UHFFFAOYSA-N indobufen Chemical compound C1=CC(C(C(O)=O)CC)=CC=C1N1C(=O)C2=CC=CC=C2C1 AYDXAULLCROVIT-UHFFFAOYSA-N 0.000 description 2
229960003422 indobufen Drugs 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
BUBRUAQVAPTGHV-UHFFFAOYSA-N n,n-diethyl-2-nitroaniline Chemical compound CCN(CC)C1=CC=CC=C1[N+]([O-])=O BUBRUAQVAPTGHV-UHFFFAOYSA-N 0.000 description 2
239000003444 phase transfer catalyst Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
150000005188 1,2,4-trinitrobenzenes Chemical class 0.000 description 1
OVSLGPPAAYJIGH-UHFFFAOYSA-N 1,2-dibutyl-4-nitrobenzene Chemical compound CCCCC1=CC=C([N+]([O-])=O)C=C1CCCC OVSLGPPAAYJIGH-UHFFFAOYSA-N 0.000 description 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
TUEWNQTZFYCGPG-UHFFFAOYSA-N 1,3-diethyl-2-nitrobenzene Chemical class CCC1=CC=CC(CC)=C1[N+]([O-])=O TUEWNQTZFYCGPG-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UPKQTNZSDMAYNO-UHFFFAOYSA-N 1-benzyl-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1CC1=CC=CC=C1 UPKQTNZSDMAYNO-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
VNHGETRQQSYUGZ-UHFFFAOYSA-N 1-nitro-2-phenoxybenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1 VNHGETRQQSYUGZ-UHFFFAOYSA-N 0.000 description 1
VDTUSEIYUROSGJ-UHFFFAOYSA-N 1-nitroisoquinoline Chemical class C1=CC=C2C([N+](=O)[O-])=NC=CC2=C1 VDTUSEIYUROSGJ-UHFFFAOYSA-N 0.000 description 1
RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical class C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 1
XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 1
VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 description 1
BQJBLKLVWWJESU-UHFFFAOYSA-N 2-(1,3-dihydropyrazol-2-yl)-2-phenylacetic acid Chemical class C=1C=CC=CC=1C(C(=O)O)N1CC=CN1 BQJBLKLVWWJESU-UHFFFAOYSA-N 0.000 description 1
AJUIWIYLSGYVRQ-UHFFFAOYSA-N 2-(3-chloro-4-nitrophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C([N+]([O-])=O)C(Cl)=C1 AJUIWIYLSGYVRQ-UHFFFAOYSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
FWYNCHBBDIJSRE-UHFFFAOYSA-N 2-chloro-2-cyclohexylacetonitrile Chemical compound N#CC(Cl)C1CCCCC1 FWYNCHBBDIJSRE-UHFFFAOYSA-N 0.000 description 1
WZSOEUAQKKEHFE-UHFFFAOYSA-N 2-chloro-2-phenylacetonitrile Chemical compound N#CC(Cl)C1=CC=CC=C1 WZSOEUAQKKEHFE-UHFFFAOYSA-N 0.000 description 1
YYJUXSGXHHPBTK-UHFFFAOYSA-N 2-chloro-3-(3-chloro-2-methylphenyl)propanenitrile Chemical compound CC1=C(Cl)C=CC=C1CC(Cl)C#N YYJUXSGXHHPBTK-UHFFFAOYSA-N 0.000 description 1
ZUPBNBYEVVGQKK-UHFFFAOYSA-N 2-chloro-3-phenylpropanenitrile Chemical compound N#CC(Cl)CC1=CC=CC=C1 ZUPBNBYEVVGQKK-UHFFFAOYSA-N 0.000 description 1
WTDNWEITCUMXGW-UHFFFAOYSA-N 2-chlorobutanenitrile Chemical compound CCC(Cl)C#N WTDNWEITCUMXGW-UHFFFAOYSA-N 0.000 description 1
ATVDTOOBVYNLKI-UHFFFAOYSA-N 2-chlorohexanenitrile Chemical compound CCCCC(Cl)C#N ATVDTOOBVYNLKI-UHFFFAOYSA-N 0.000 description 1
MBCBZYXBXWRQCW-UHFFFAOYSA-N 2-chloropent-4-enenitrile Chemical compound N#CC(Cl)CC=C MBCBZYXBXWRQCW-UHFFFAOYSA-N 0.000 description 1
MHMIICKCHQITOX-UHFFFAOYSA-N 2-chloropentanenitrile Chemical compound CCCC(Cl)C#N MHMIICKCHQITOX-UHFFFAOYSA-N 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
QDACQOOLIVCDNP-UHFFFAOYSA-N 2-nitro-1-oxidopyridin-1-ium Chemical compound [O-][N+](=O)C1=CC=CC=[N+]1[O-] QDACQOOLIVCDNP-UHFFFAOYSA-N 0.000 description 1
DBMPHBQSQZZRDP-UHFFFAOYSA-N 2-nitro-2-phenylacetonitrile Chemical class [O-][N+](=O)C(C#N)C1=CC=CC=C1 DBMPHBQSQZZRDP-UHFFFAOYSA-N 0.000 description 1
UDAIGHZFMLGNDQ-UHFFFAOYSA-N 2-nitroquinoline Chemical class C1=CC=CC2=NC([N+](=O)[O-])=CC=C21 UDAIGHZFMLGNDQ-UHFFFAOYSA-N 0.000 description 1
JIZRGGUCOQKGQD-UHFFFAOYSA-N 2-nitrothiophene Chemical class [O-][N+](=O)C1=CC=CS1 JIZRGGUCOQKGQD-UHFFFAOYSA-N 0.000 description 1
PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
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CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
BAJQRLZAPXASRD-UHFFFAOYSA-N 4-Nitrobiphenyl Chemical group C1=CC([N+](=O)[O-])=CC=C1C1=CC=CC=C1 BAJQRLZAPXASRD-UHFFFAOYSA-N 0.000 description 1
PYGMPFQCCWBTJQ-UHFFFAOYSA-N 5-nitroisoquinoline Chemical compound N1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 PYGMPFQCCWBTJQ-UHFFFAOYSA-N 0.000 description 1
SMHPLBXIVNQFBA-UHFFFAOYSA-N 6-nitroquinoline Chemical class N1=CC=CC2=CC([N+](=O)[O-])=CC=C21 SMHPLBXIVNQFBA-UHFFFAOYSA-N 0.000 description 1
101150034533 ATIC gene Proteins 0.000 description 1
241000427202 Adria Species 0.000 description 1
KCMZYCFSSYXEQR-UHFFFAOYSA-N CCCC[K] Chemical compound CCCC[K] KCMZYCFSSYXEQR-UHFFFAOYSA-N 0.000 description 1
NTZRDKVFLPLTPU-UHFFFAOYSA-N CC[Na] Chemical compound CC[Na] NTZRDKVFLPLTPU-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
STZZWJCGRKXEFF-UHFFFAOYSA-N Dichloroacetonitrile Chemical compound ClC(Cl)C#N STZZWJCGRKXEFF-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
IDSGFSCSMXRJON-UHFFFAOYSA-N N-Carbamyl-L-glutamicacid Chemical class C1=CC([N+](=O)[O-])=CC=C1CC1=CC=CC=C1 IDSGFSCSMXRJON-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
238000006127 Vicarious substitution reaction Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000004171 alkoxy aryl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000004659 aryl alkyl thio group Chemical group 0.000 description 1
125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
125000005110 aryl thio group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
229940045348 brown mixture Drugs 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
125000005366 cycloalkylthio group Chemical group 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229960002390 flurbiprofen Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000004995 haloalkylthio group Chemical group 0.000 description 1
125000004996 haloaryloxy group Chemical group 0.000 description 1
125000006769 halocycloalkoxy group Chemical group 0.000 description 1
125000005347 halocycloalkyl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
239000012035 limiting reagent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
MWKRYWHVFDEPST-UHFFFAOYSA-N n-ethyl-2-nitro-n-phenylacetamide Chemical class [O-][N+](=O)CC(=O)N(CC)C1=CC=CC=C1 MWKRYWHVFDEPST-UHFFFAOYSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
239000012450 pharmaceutical intermediate Substances 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
PIDSZXPFGCURGN-UHFFFAOYSA-N pirprofen Chemical compound ClC1=CC(C(C(O)=O)C)=CC=C1N1CC=CC1 PIDSZXPFGCURGN-UHFFFAOYSA-N 0.000 description 1
229960000851 pirprofen Drugs 0.000 description 1
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
229910001950 potassium oxide Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
KBGJIKKXNIQHQH-UHFFFAOYSA-N potassium;methanidylbenzene Chemical compound [K+].[CH2-]C1=CC=CC=C1 KBGJIKKXNIQHQH-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229940083608 sodium hydroxide Drugs 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
CWXOAQXKPAENDI-UHFFFAOYSA-N sodium methylsulfinylmethylide Chemical compound [Na+].CS([CH2-])=O CWXOAQXKPAENDI-UHFFFAOYSA-N 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
ONQCKWIDZTZEJA-UHFFFAOYSA-N sodium;pentane Chemical compound [Na+].CCCC[CH2-] ONQCKWIDZTZEJA-UHFFFAOYSA-N 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
230000002194 synthesizing effect Effects 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
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
150000005186 trinitrobenzenes Chemical class 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000414303A 1981-11-02 1982-10-27 Methode de substitution nucleophile Expired CA1177086A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/317,321 US4370278A (en)	1981-11-02	1981-11-02	Nucleophilic substitution process
US317,321		1981-11-02
US41155482A	1982-08-25	1982-08-25
US411,554		1982-08-25

Publications (1)

Publication Number	Publication Date
CA1177086A true CA1177086A (fr)	1984-10-30

Family

ID=26980891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000414303A Expired CA1177086A (fr)	1981-11-02	1982-10-27	Methode de substitution nucleophile

Country Status (1)

Country	Link
CA (1)	CA1177086A (fr)

1982
- 1982-10-27 CA CA000414303A patent/CA1177086A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-10-31	MKEC	Expiry (correction)
2002-10-27	MKEX	Expiry

Publication	Publication Date	Title
RajanBabu et al.	1985	Nucleophilic addition of silyl enol ethers to aromatic nitro compounds: scope and mechanism of reaction
Liotta et al.	1983	Simple, inexpensive procedure for the large-scale production of alkyl quinones
US3847990A (en)	1974-11-12	Process for the production of nitrodiphenyl amine derivatives
US4370278A (en)	1983-01-25	Nucleophilic substitution process
CA1177086A (fr)	1984-10-30	Methode de substitution nucleophile
US5254776A (en)	1993-10-19	Synthesis of bromobiphenyls
Skiles et al.	1979	Subsessiline: structure revision and synthesis
EP0078709B1 (fr)	1986-10-01	Préparation de nitroalkylcyanides et leurs dérivés
JP2004516309A (ja)	2004-06-03	１，５−ナフタレンジアミンの製造方法
EP0077662B1 (fr)	1985-10-02	Préparation d'esters de l'acide nitroarylacétique et leurs dérivés
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JP3663229B2 (ja)	2005-06-22	４−ハロ−２′−ニトロブチロフエノン化合物の製造方法
US4476315A (en)	1984-10-09	Nucleophilic substitution process
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US4499026A (en)	1985-02-12	Nucleophilic substitution process
US4266069A (en)	1981-05-05	Processes for the preparation of hydratropic acids and esters
US4502996A (en)	1985-03-05	Nucleophilic substitution process
US4567280A (en)	1986-01-28	Process for producing iodo-aromatic compounds
Johnson et al.	1981	Syntheses of amine derivatives of phencyclidine
US4581463A (en)	1986-04-08	Nucleophilic substitution process combined with additional reaction steps
US4710581A (en)	1987-12-01	Nucleophilic substitution process
Raphael et al.	1988	Synthesis of indolin-2-ones (oxindoles) related to mitomycin A
CN102180794B (zh)	2013-11-06	一种硝基苯类化合物的合成方法
EP0032620A1 (fr)	1981-07-29	Procédé pour la préparation d'esters de l'acide 2-arylpropioniques thérapeutiques, et nouveaux esters arylmethylmalonates