RU1773259C - Способ получени анилинофумарата - Google Patents
Способ получени анилинофумаратаInfo
- Publication number
- RU1773259C RU1773259C SU884356526A SU4356526A RU1773259C RU 1773259 C RU1773259 C RU 1773259C SU 884356526 A SU884356526 A SU 884356526A SU 4356526 A SU4356526 A SU 4356526A RU 1773259 C RU1773259 C RU 1773259C
- Authority
- RU
- Russia
- Prior art keywords
- aniline
- bisulfate
- chloride
- base
- dichlorosuccinate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 title abstract description 3
- 238000003786 synthesis reaction Methods 0.000 title abstract description 3
- 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 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 7
- XSCRWBSKSVOZOK-UHFFFAOYSA-N 2,3-dichlorobutanedioic acid Chemical compound OC(=O)C(Cl)C(Cl)C(O)=O XSCRWBSKSVOZOK-UHFFFAOYSA-N 0.000 claims abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims abstract description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims abstract description 5
- RXUORJSZMBEMGC-WLHGVMLRSA-N aniline (E)-but-2-enedioic acid Chemical compound Nc1ccccc1.OC(=O)\C=C\C(O)=O RXUORJSZMBEMGC-WLHGVMLRSA-N 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 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 claims abstract description 3
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000003993 interaction Effects 0.000 claims abstract description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 3
- 235000011181 potassium carbonates Nutrition 0.000 claims abstract description 3
- 235000015424 sodium Nutrition 0.000 claims abstract description 3
- DHAWHVVWUNNONG-UHFFFAOYSA-M tributyl(methyl)azanium;bromide Chemical compound [Br-].CCCC[N+](C)(CCCC)CCCC DHAWHVVWUNNONG-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims 1
- 125000005208 trialkylammonium group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 abstract description 3
- 230000002363 herbicidal effect Effects 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PBGMSGHICSEALQ-UHFFFAOYSA-N diethyl 2,3-dichlorobutanedioate Chemical compound CCOC(=O)C(Cl)C(Cl)C(=O)OCC PBGMSGHICSEALQ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 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 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Classifications
-
- 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
- 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
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)
- Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Control Of Transmission Device (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/101,453 US4814486A (en) | 1987-10-01 | 1987-10-01 | Method for the preparation of anilinofumarate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU1773259C true RU1773259C (ru) | 1992-10-30 |
Family
ID=22284722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU884356526A RU1773259C (ru) | 1987-10-01 | 1988-09-30 | Способ получени анилинофумарата |
Country Status (22)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4910327A (en) * | 1982-05-25 | 1990-03-20 | American Cyanamid Company | Alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid: dialkyl 3-(substituted)phenylaminobut-2-ene-dioates and methods for the preparation thereof |
| US5001254A (en) * | 1986-08-29 | 1991-03-19 | American Cyanamid Co | Novel method for the preparation of quinoline-2,3-dicarboxylic |
| US4904816A (en) * | 1989-06-15 | 1990-02-27 | American Cyanamid Company | Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures thereof |
| EP2105432A1 (en) * | 2002-02-28 | 2009-09-30 | Sumitomo Chemical Company, Limited | Process for Producing Chromone Compound |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4638068A (en) * | 1981-04-09 | 1987-01-20 | American Cyanamid Company | 2-(2-imidazolin-2-yl)-pyridines and quinolines, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
| US4518780A (en) * | 1982-05-25 | 1985-05-21 | American Cyanamid Company | Process for the preparation of 2-(5,5-disubstituted-4-oxo-2-imidazolin-2-yl)nicotinic acids and quinoline-3-carboxylic acids |
| 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 |
| US4459409A (en) * | 1982-05-25 | 1984-07-10 | American Cyanamid Company | Process for the preparation of 2,3-quinolinedicarboxylic acids |
| DE3765899D1 (de) * | 1986-08-29 | 1990-12-06 | American Cyanamid Co | Verfahren zur herstellung von anilinofumarat und 2,3-chinolindicarbonsaeure. |
| US4675432A (en) * | 1986-08-29 | 1987-06-23 | American Cyanamid Company | Method for the preparation of anilinofumarate |
-
1987
- 1987-10-01 US US07/101,453 patent/US4814486A/en not_active Expired - Lifetime
-
1988
- 1988-08-16 DE DE8888113254T patent/DE3878122T2/de not_active Expired - Fee Related
- 1988-08-16 ES ES198888113254T patent/ES2039525T3/es not_active Expired - Lifetime
- 1988-08-16 AT AT88113254T patent/ATE85321T1/de not_active IP Right Cessation
- 1988-08-16 EP EP88113254A patent/EP0309711B1/en not_active Expired - Lifetime
- 1988-08-24 IL IL87546A patent/IL87546A0/xx not_active IP Right Cessation
- 1988-09-27 RO RO1988135289A patent/RO101205B1/ro unknown
- 1988-09-27 JP JP63239872A patent/JP2703573B2/ja not_active Expired - Lifetime
- 1988-09-29 CA CA000578776A patent/CA1297126C/en not_active Expired - Lifetime
- 1988-09-29 DD DD88320260A patent/DD275453A5/de unknown
- 1988-09-30 ZA ZA887372A patent/ZA887372B/xx unknown
- 1988-09-30 BR BR8805058A patent/BR8805058A/pt not_active IP Right Cessation
- 1988-09-30 YU YU1837/88A patent/YU45062B/xx unknown
- 1988-09-30 RU SU884356526A patent/RU1773259C/ru active
- 1988-09-30 AR AR88312093A patent/AR244658A1/es active
- 1988-09-30 CS CS886510A patent/CS275946B6/cs not_active IP Right Cessation
- 1988-09-30 IE IE296288A patent/IE63235B1/en not_active IP Right Cessation
- 1988-09-30 KR KR1019880012832A patent/KR970006470B1/ko not_active Expired - Fee Related
- 1988-09-30 HU HU885099A patent/HU200592B/hu not_active IP Right Cessation
- 1988-09-30 BG BG085574A patent/BG47347A3/xx unknown
- 1988-09-30 AU AU23304/88A patent/AU611952B2/en not_active Ceased
-
1993
- 1993-02-04 GR GR920402264T patent/GR3006960T3/el unknown
Non-Patent Citations (1)
| Title |
|---|
| Патент US № 4675432.кл. 560-44, 1987. * |
Also Published As
| Publication number | Publication date |
|---|---|
| HU200592B (en) | 1990-07-28 |
| YU183788A (en) | 1990-02-28 |
| ES2039525T3 (es) | 1993-10-01 |
| BR8805058A (pt) | 1989-05-09 |
| CA1297126C (en) | 1992-03-10 |
| KR890006570A (ko) | 1989-06-14 |
| DD275453A5 (de) | 1990-01-24 |
| ZA887372B (en) | 1989-06-28 |
| EP0309711A1 (en) | 1989-04-05 |
| ATE85321T1 (de) | 1993-02-15 |
| IL87546A0 (en) | 1989-01-31 |
| HUT48573A (en) | 1989-06-28 |
| YU45062B (en) | 1991-06-30 |
| CS275946B6 (en) | 1992-03-18 |
| RO101205B1 (en) | 1992-01-28 |
| DE3878122T2 (de) | 1993-05-27 |
| IE882962L (en) | 1989-04-01 |
| GR3006960T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-06-30 |
| US4814486A (en) | 1989-03-21 |
| IE63235B1 (en) | 1995-04-05 |
| EP0309711B1 (en) | 1993-02-03 |
| DE3878122D1 (de) | 1993-03-18 |
| AU611952B2 (en) | 1991-06-27 |
| AU2330488A (en) | 1989-04-06 |
| KR970006470B1 (ko) | 1997-04-28 |
| JP2703573B2 (ja) | 1998-01-26 |
| JPH01113352A (ja) | 1989-05-02 |
| BG47347A3 (en) | 1990-06-15 |
| AR244658A1 (es) | 1993-11-30 |
| CS8806510A2 (en) | 1991-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| REG | Reference to a code of a succession state |
Ref country code: RU Ref legal event code: MM4A Effective date: 20041001 |