IL92786A - Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures therof - Google Patents

Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures therof

Info

Publication number: IL92786A
Authority: IL; Israel
Prior art keywords: chloromaleate; anilinofumarate; formula; chlorofumarate; manufacture
Prior art date: 1989-06-15

Application number

IL9278689A

Other languages

English (en)

Other versions

IL92786A0 (en

Original Assignee

American Cyanamid Co

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.)

1989-06-15

Filing date

1989-12-18

Publication date

1994-05-30

1989-12-18 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1990-09-17 Publication of IL92786A0 publication Critical patent/IL92786A0/xx

1994-05-30 Publication of IL92786A publication Critical patent/IL92786A/en

Links

238000000034 method Methods 0.000 title claims abstract description 17
XQRVITDMGTWTIC-VURMDHGXSA-N (Z)-2-anilinobut-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)/NC1=CC=CC=C1 XQRVITDMGTWTIC-VURMDHGXSA-N 0.000 title claims abstract description 14
ZQHJVIHCDHJVII-OWOJBTEDSA-N (e)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(\Cl)C(O)=O ZQHJVIHCDHJVII-OWOJBTEDSA-N 0.000 title claims abstract description 9
239000000203 mixture Substances 0.000 title claims abstract description 9
ZQHJVIHCDHJVII-UPHRSURJSA-N (z)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(/Cl)C(O)=O ZQHJVIHCDHJVII-UPHRSURJSA-N 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title abstract description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 10
239000002585 base Substances 0.000 claims description 8
239000003444 phase transfer catalyst Substances 0.000 claims description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
239000007864 aqueous solution Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims description 2
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
MDDBCVZNWKPLAD-VOTSOKGWSA-N (E)-4-anilinooxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)ONC1=CC=CC=C1 MDDBCVZNWKPLAD-VOTSOKGWSA-N 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
VOEQTGMCAHZUNJ-AATRIKPKSA-N diethyl (e)-2-chlorobut-2-enedioate Chemical group CCOC(=O)\C=C(\Cl)C(=O)OCC VOEQTGMCAHZUNJ-AATRIKPKSA-N 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000047 product Substances 0.000 description 5
238000004458 analytical method Methods 0.000 description 4
238000010586 diagram Methods 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
ROMURMXNNUEGCC-BENRWUELSA-N diethyl (z)-2-anilinobut-2-enedioate Chemical compound CCOC(=O)\C=C(C(=O)OCC)/NC1=CC=CC=C1 ROMURMXNNUEGCC-BENRWUELSA-N 0.000 description 3
238000001030 gas--liquid chromatography Methods 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
YHUVMHKAHWKQBI-UHFFFAOYSA-N quinoline-2,3-dicarboxylic acid Chemical compound C1=CC=C2N=C(C(O)=O)C(C(=O)O)=CC2=C1 YHUVMHKAHWKQBI-UHFFFAOYSA-N 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
238000001816 cooling Methods 0.000 description 2
VOEQTGMCAHZUNJ-WAYWQWQTSA-N diethyl (z)-2-chlorobut-2-enedioate Chemical compound CCOC(=O)\C=C(/Cl)C(=O)OCC VOEQTGMCAHZUNJ-WAYWQWQTSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
KWMCUYXCRJIEQH-WAYWQWQTSA-N (Z)-2-(2-chloroethyl)-3-ethylbut-2-enedioic acid Chemical compound CC\C(C(O)=O)=C(C(O)=O)/CCCl KWMCUYXCRJIEQH-WAYWQWQTSA-N 0.000 description 1
PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 1
ZVWKLNLSZUQCNV-UHFFFAOYSA-N 4,5-diethylquinoline-2,3-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(CC)=C2C(CC)=CC=CC2=N1 ZVWKLNLSZUQCNV-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000701796 Fowl aviadenovirus 1 Species 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
AXNMAXJLFCOHRR-UHFFFAOYSA-N P(=O)(Cl)(Cl)Cl.N(C1=CC=CC=C1)/C(/C(=O)O)=CC(=O)O Chemical compound P(=O)(Cl)(Cl)Cl.N(C1=CC=CC=C1)/C(/C(=O)O)=CC(=O)O AXNMAXJLFCOHRR-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
YDUFFDZHKJIGDK-AUNBPGBOSA-M [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl/C(/C(=O)OCC)=C/C(=O)OCC Chemical compound [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl/C(/C(=O)OCC)=C/C(=O)OCC YDUFFDZHKJIGDK-AUNBPGBOSA-M 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
ICMBEQVDQPLOFB-UHFFFAOYSA-N diethyl quinoline-2,3-dicarboxylate Chemical compound C1=CC=C2N=C(C(=O)OCC)C(C(=O)OCC)=CC2=C1 ICMBEQVDQPLOFB-UHFFFAOYSA-N 0.000 description 1
229960004756 ethanol Drugs 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/30—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Color Printing (AREA)

IL9278689A 1989-06-15 1989-12-18 Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures therof IL92786A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/366,554 US4904816A (en)	1989-06-15	1989-06-15	Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures thereof

Publications (2)

Publication Number	Publication Date
IL92786A0 IL92786A0 (en)	1990-09-17
IL92786A true IL92786A (en)	1994-05-30

Family

ID=23443514

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9278689A IL92786A (en)	1989-06-15	1989-12-18	Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures therof

Country Status (16)

Country	Link
US (1)	US4904816A (fr)
EP (1)	EP0402561B1 (fr)
JP (1)	JP2812761B2 (fr)
KR (1)	KR100207247B1 (fr)
AR (1)	AR245437A1 (fr)
AT (1)	ATE112548T1 (fr)
AU (1)	AU617576B2 (fr)
BR (1)	BR9000119A (fr)
CA (1)	CA2007653C (fr)
DE (1)	DE69013062T2 (fr)
DK (1)	DK0402561T3 (fr)
ES (1)	ES2060819T3 (fr)
HU (1)	HU204771B (fr)
IE (1)	IE64431B1 (fr)
IL (1)	IL92786A (fr)
ZA (1)	ZA90100B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5276157A (en) *	1991-12-20	1994-01-04	American Cyanamid Company	Process for the purification of 2,3-pyridine and quinolinedicarboxylic acid diester compounds
CN109187521A (zh) *	2018-08-30	2019-01-11	湖南博隽生物医药有限公司	一种检测唾液中酒精含量的聚合物膜及其制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD71545A (fr) *
US4656283A (en) *	1982-05-25	1987-04-07	American Cyanamid Company	Alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid
US4843162A (en) *	1982-05-25	1989-06-27	American Cyanamid Company	Alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid
US4675432A (en) *	1986-08-29	1987-06-23	American Cyanamid Company	Method for the preparation of anilinofumarate
DE3765899D1 (de) *	1986-08-29	1990-12-06	American Cyanamid Co	Verfahren zur herstellung von anilinofumarat und 2,3-chinolindicarbonsaeure.
US4814486A (en) *	1987-10-01	1989-03-21	American Cyanamid Company	Method for the preparation of anilinofumarate

1989
- 1989-06-15 US US07/366,554 patent/US4904816A/en not_active Expired - Lifetime
- 1989-12-18 IL IL9278689A patent/IL92786A/en not_active IP Right Cessation
1990
- 1990-01-05 ZA ZA90100A patent/ZA90100B/xx unknown
- 1990-01-08 AR AR90315897A patent/AR245437A1/es active
- 1990-01-11 JP JP2002661A patent/JP2812761B2/ja not_active Expired - Fee Related
- 1990-01-12 IE IE13390A patent/IE64431B1/en not_active IP Right Cessation
- 1990-01-12 EP EP90100632A patent/EP0402561B1/fr not_active Expired - Lifetime
- 1990-01-12 ES ES90100632T patent/ES2060819T3/es not_active Expired - Lifetime
- 1990-01-12 CA CA002007653A patent/CA2007653C/fr not_active Expired - Fee Related
- 1990-01-12 DE DE69013062T patent/DE69013062T2/de not_active Expired - Fee Related
- 1990-01-12 HU HU90120A patent/HU204771B/hu not_active IP Right Cessation
- 1990-01-12 BR BR909000119A patent/BR9000119A/pt not_active IP Right Cessation
- 1990-01-12 DK DK90100632.0T patent/DK0402561T3/da active
- 1990-01-12 AT AT90100632T patent/ATE112548T1/de not_active IP Right Cessation
- 1990-01-12 AU AU47929/90A patent/AU617576B2/en not_active Ceased
- 1990-01-13 KR KR1019900000384A patent/KR100207247B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AR245437A1 (es)	1994-01-31
CA2007653A1 (fr)	1990-12-15
BR9000119A (pt)	1991-10-08
HUT54101A (en)	1991-01-28
IL92786A0 (en)	1990-09-17
JP2812761B2 (ja)	1998-10-22
HU900120D0 (en)	1990-03-28
ZA90100B (en)	1990-10-31
AU617576B2 (en)	1991-11-28
EP0402561B1 (fr)	1994-10-05
DE69013062T2 (de)	1995-05-11
CA2007653C (fr)	1999-04-06
KR910001563A (ko)	1991-01-31
HU204771B (en)	1992-02-28
AU4792990A (en)	1990-12-20
IE900133L (en)	1990-12-15
US4904816A (en)	1990-02-27
ATE112548T1 (de)	1994-10-15
ES2060819T3 (es)	1994-12-01
IE900133A1 (en)	1991-01-02
EP0402561A2 (fr)	1990-12-19
DE69013062D1 (de)	1994-11-10
KR100207247B1 (ko)	1999-07-15
DK0402561T3 (da)	1994-10-31
EP0402561A3 (fr)	1991-05-29
IE64431B1 (en)	1995-08-09
JPH0324045A (ja)	1991-02-01

Legal Events

Date	Code	Title
2000-06-29	KB	Patent renewed
2004-02-08	KB	Patent renewed
2008-01-22	KB	Patent renewed
2010-11-30	EXP	Patent expired

Publication	Publication Date	Title
WO2000062782A1 (fr)	2000-10-26	Nouvelle synthese et cristallisation de composes contenant de la piperazine
US4904816A (en)	1990-02-27	Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures thereof
KR100656636B1 (ko)	2006-12-11	6-메틸-2-(4-메틸-페닐)-이미다조[1,2-ａ]피리딘-3-(Ｎ,Ｎ-디메틸-아세트아미드) 및 중간체의 제조 방법
US6576764B2 (en)	2003-06-10	Synthesis and crystallization of piperazine ring-containing compounds
US5233082A (en)	1993-08-03	Method of making 3-hydroxy-2,4,5-trifluorobenzoic acid
EP0388620B1 (fr)	1994-11-02	Procédé pour la préparation de o-carboxypyridyl- et de o-carboxyquinolylimidazolinones
JPH06199759A (ja)	1994-07-19	フェニル酢酸誘導体の製造方法
EP0309711B1 (fr)	1993-02-03	Méthode pour la préparation d'anilinofumarates
EP0262305B1 (fr)	1990-10-31	Procédé pour la préparation d'anilinofumarate et de l'acide quinoléine-dicarboxylique-2,3
EP0548560B1 (fr)	1996-01-10	Procédé de fabrication d'esters d'acide halomaléique et halofumarique
KR890001241B1 (ko)	1989-04-28	4-아세틸 이소퀴놀리논 화합물의 제조방법
US4847405A (en)	1989-07-11	Method for the preparation of anilinofumarate [quinoline-2,3- dicarboxylic]
US4758679A (en)	1988-07-19	Preparation of 7-(3-(propylamino)-2-hydroxypropoxy)flavone
US20040176591A1 (en)	2004-09-09	Novel synthesis and crystallization of peperazine ring-containing compounds
JPH02218666A (ja)	1990-08-31	２―クロロ―５―クロロメチルピリジンの製造方法
GB2291421A (en)	1996-01-24	A process for preparing a quinoline carboxylic acid
JPH0583537B2 (fr)	1993-11-26
JPS6087267A (ja)	1985-05-16	４―キノリノン類の製造方法
JPH0432824B2 (fr)	1992-06-01
JPS6249271B2 (fr)	1987-10-19
JPH0250104B2 (fr)	1990-11-01
JPH0211569A (ja)	1990-01-16	高純度２−クロロ−６−メチルアミノピリジンの製造方法
JPWO1995023787A1 (ja)	1996-08-27	５，７−ジクロロ−４−ヒドロキシキノリンの製造方法