IL102191A - Method for the preparation of alkyl 3-chloroanthranilates - Google Patents
Method for the preparation of alkyl 3-chloroanthranilatesInfo
- Publication number
- IL102191A IL102191A IL10219192A IL10219192A IL102191A IL 102191 A IL102191 A IL 102191A IL 10219192 A IL10219192 A IL 10219192A IL 10219192 A IL10219192 A IL 10219192A IL 102191 A IL102191 A IL 102191A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- chloroanthranilate
- chloro
- mixture
- chloroanthranilates
- Prior art date
Links
- -1 alkyl 3-chloroanthranilates Chemical class 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 7
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims abstract description 16
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 9
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims abstract description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- LWUAMROXVQLJKA-UHFFFAOYSA-N 2-amino-3-chlorobenzoic acid Chemical compound NC1=C(Cl)C=CC=C1C(O)=O LWUAMROXVQLJKA-UHFFFAOYSA-N 0.000 claims description 11
- IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical class NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 150000008282 halocarbons Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 abstract description 14
- 230000021736 acetylation Effects 0.000 abstract description 3
- 238000006640 acetylation reaction Methods 0.000 abstract description 3
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 6
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 5
- 229940102398 methyl anthranilate Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PZRSRAUPUQOYQX-UHFFFAOYSA-N 3-bromopiperidin-4-one Chemical compound BrC1CNCCC1=O PZRSRAUPUQOYQX-UHFFFAOYSA-N 0.000 description 2
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KTHTXLUIEAIGCD-UHFFFAOYSA-N 2-amino-3,5-dichlorobenzoic acid Chemical compound NC1=C(Cl)C=C(Cl)C=C1C(O)=O KTHTXLUIEAIGCD-UHFFFAOYSA-N 0.000 description 1
- UERPUZBSSSAZJE-UHFFFAOYSA-N 3-chlorophthalic anhydride Chemical compound ClC1=CC=CC2=C1C(=O)OC2=O UERPUZBSSSAZJE-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000003683 electrophilic halogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- TVAAIYFBEWHVCV-UHFFFAOYSA-N methyl 2-acetamido-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NC(C)=O TVAAIYFBEWHVCV-UHFFFAOYSA-N 0.000 description 1
- MSXSZFYRADEEJA-UHFFFAOYSA-N methyl 2-amino-3-chlorobenzoate Chemical compound COC(=O)C1=CC=CC(Cl)=C1N MSXSZFYRADEEJA-UHFFFAOYSA-N 0.000 description 1
- 235000020573 organic concentrate Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
- C07C229/58—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of a six-membered aromatic ring, e.g. N-phenyl-anthranilic acids
-
- 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
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/715,514 US5118832A (en) | 1991-06-14 | 1991-06-14 | Process for the preparation of alkyl 3-chloroanthranilates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL102191A0 IL102191A0 (en) | 1993-01-14 |
| IL102191A true IL102191A (en) | 1996-10-31 |
Family
ID=24874341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10219192A IL102191A (en) | 1991-06-14 | 1992-06-12 | Method for the preparation of alkyl 3-chloroanthranilates |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5118832A (de) |
| EP (1) | EP0518374B1 (de) |
| JP (1) | JP3268825B2 (de) |
| KR (1) | KR100228368B1 (de) |
| AT (1) | ATE137492T1 (de) |
| AU (1) | AU641097B2 (de) |
| CA (1) | CA2071118C (de) |
| DE (1) | DE69210309T2 (de) |
| DK (1) | DK0518374T3 (de) |
| ES (1) | ES2086581T3 (de) |
| HU (1) | HU209738B (de) |
| IL (1) | IL102191A (de) |
| RU (1) | RU2026284C1 (de) |
| TW (1) | TW204335B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5118832A (en) * | 1991-06-14 | 1992-06-02 | Dowelanco | Process for the preparation of alkyl 3-chloroanthranilates |
| DE4313174A1 (de) * | 1993-04-22 | 1994-10-27 | Hoechst Ag | Verfahren zur Herstellung von 3-Chloranthranilsäurealkylestern hoher Reinheit aus 3-Chloranthranilsäure |
| CN103193666B (zh) * | 2013-04-09 | 2015-11-18 | 江苏省农用激素工程技术研究中心有限公司 | 2-氨基-3-氯苯甲酸甲酯的制备方法 |
| EP3015453B1 (de) * | 2014-10-28 | 2016-10-12 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Verfahren zur Herstellung von Clomiphen |
| EP3368506B1 (de) | 2016-04-22 | 2023-09-06 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Verfahren zur herstellung von enclomiphencitrat mit nadelförmigem kristallhabitus |
| CN107266324A (zh) * | 2017-07-17 | 2017-10-20 | 常州大学 | 一种2‑氨基‑3‑氯苯甲酸甲酯的合成方法 |
| CN108047069A (zh) * | 2017-12-29 | 2018-05-18 | 南通泰禾化工股份有限公司 | 一种2-氨基-3-氯苯甲酸甲酯的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8006496A (nl) * | 1979-12-19 | 1981-07-16 | Upjohn Co | Werkwijze voor het bereiden van arylpropionzuren. |
| US5118832A (en) * | 1991-06-14 | 1992-06-02 | Dowelanco | Process for the preparation of alkyl 3-chloroanthranilates |
-
1991
- 1991-06-14 US US07/715,514 patent/US5118832A/en not_active Expired - Fee Related
-
1992
- 1992-06-10 JP JP17500092A patent/JP3268825B2/ja not_active Expired - Fee Related
- 1992-06-11 AU AU18139/92A patent/AU641097B2/en not_active Ceased
- 1992-06-12 DK DK92109952.9T patent/DK0518374T3/da active
- 1992-06-12 DE DE69210309T patent/DE69210309T2/de not_active Expired - Fee Related
- 1992-06-12 EP EP92109952A patent/EP0518374B1/de not_active Expired - Lifetime
- 1992-06-12 IL IL10219192A patent/IL102191A/en not_active IP Right Cessation
- 1992-06-12 ES ES92109952T patent/ES2086581T3/es not_active Expired - Lifetime
- 1992-06-12 KR KR1019920010208A patent/KR100228368B1/ko not_active Expired - Fee Related
- 1992-06-12 HU HU9201972A patent/HU209738B/hu not_active IP Right Cessation
- 1992-06-12 CA CA002071118A patent/CA2071118C/en not_active Expired - Fee Related
- 1992-06-12 AT AT92109952T patent/ATE137492T1/de not_active IP Right Cessation
- 1992-06-12 RU SU925011910A patent/RU2026284C1/ru active
- 1992-06-13 TW TW081104644A patent/TW204335B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| JP3268825B2 (ja) | 2002-03-25 |
| DE69210309D1 (de) | 1996-06-05 |
| KR930000466A (ko) | 1993-01-15 |
| DK0518374T3 (da) | 1996-08-26 |
| RU2026284C1 (ru) | 1995-01-09 |
| JPH05194341A (ja) | 1993-08-03 |
| HU9201972D0 (en) | 1992-09-28 |
| EP0518374B1 (de) | 1996-05-01 |
| KR100228368B1 (ko) | 1999-11-01 |
| DE69210309T2 (de) | 1996-09-12 |
| TW204335B (de) | 1993-04-21 |
| HUT64010A (en) | 1993-11-29 |
| US5118832A (en) | 1992-06-02 |
| EP0518374A2 (de) | 1992-12-16 |
| ATE137492T1 (de) | 1996-05-15 |
| EP0518374A3 (en) | 1993-04-28 |
| HU209738B (en) | 1994-10-28 |
| ES2086581T3 (es) | 1996-07-01 |
| CA2071118C (en) | 1996-06-18 |
| AU641097B2 (en) | 1993-09-09 |
| IL102191A0 (en) | 1993-01-14 |
| AU1813992A (en) | 1992-12-17 |
| CA2071118A1 (en) | 1992-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| RH | Patent void | ||
| MM9K | Patent not in force due to non-payment of renewal fees |