SG10201810692VA - Process to prepare 3-methyl-2-nitrobenzoic acid by air oxidation - Google Patents
Process to prepare 3-methyl-2-nitrobenzoic acid by air oxidationInfo
- Publication number
- SG10201810692VA SG10201810692VA SG10201810692VA SG10201810692VA SG10201810692VA SG 10201810692V A SG10201810692V A SG 10201810692VA SG 10201810692V A SG10201810692V A SG 10201810692VA SG 10201810692V A SG10201810692V A SG 10201810692VA SG 10201810692V A SG10201810692V A SG 10201810692VA
- Authority
- SG
- Singapore
- Prior art keywords
- methyl
- nitrobenzoic acid
- prepare
- air oxidation
- disclosed
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- DGDAVTPQCQXLGU-UHFFFAOYSA-N 5437-38-7 Chemical compound CC1=CC=CC(C(O)=O)=C1[N+]([O-])=O DGDAVTPQCQXLGU-UHFFFAOYSA-N 0.000 title abstract 3
- 230000003647 oxidation Effects 0.000 title abstract 2
- 238000007254 oxidation reaction Methods 0.000 title abstract 2
- HDFQKJQEWGVKCQ-UHFFFAOYSA-N 1,3-dimethyl-2-nitrobenzene Chemical compound CC1=CC=CC(C)=C1[N+]([O-])=O HDFQKJQEWGVKCQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
A method for preparing 3-methyl-2-nitrobenzoic acid is disclosed wherein 1,3-dimethyl- 2-nitrobenzene is combined with an oxidation catalayst in the presence of an oxygen source and an initiator, provided that less than 99% of the 1,3-dimethyl-2-nitrobenzene is oxidized. A method for preparing compounds of Formula 7 and Formula 11 is also disclosed 5 wherein the method is characterized by using 3-methyl-2-nitrobenzoic acid as prepared by the method disclosed above, wherein R 1 is C 1–C7 alkyl, C 3–C6 cycloalkyl or C 4–C7 alkylcycloalkyl. 10 NO FIGURE
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462004459P | 2014-05-29 | 2014-05-29 | |
| US201462027275P | 2014-07-22 | 2014-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG10201810692VA true SG10201810692VA (en) | 2018-12-28 |
Family
ID=53284682
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG10201810692VA SG10201810692VA (en) | 2014-05-29 | 2015-05-29 | Process to prepare 3-methyl-2-nitrobenzoic acid by air oxidation |
| SG11201609547SA SG11201609547SA (en) | 2014-05-29 | 2015-05-29 | Process to prepare 3-methyl-2-nitrobenzoic acid by air oxidation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG11201609547SA SG11201609547SA (en) | 2014-05-29 | 2015-05-29 | Process to prepare 3-methyl-2-nitrobenzoic acid by air oxidation |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US9828328B2 (en) |
| EP (1) | EP3148962B1 (en) |
| JP (1) | JP6611735B2 (en) |
| KR (1) | KR20230052989A (en) |
| CN (2) | CN116283596A (en) |
| AU (1) | AU2015266819B2 (en) |
| BR (1) | BR112016027556B1 (en) |
| HU (1) | HUE050832T2 (en) |
| IL (1) | IL248796B (en) |
| MX (1) | MX2016015454A (en) |
| PL (1) | PL3148962T3 (en) |
| RU (1) | RU2689126C2 (en) |
| SG (2) | SG10201810692VA (en) |
| TW (1) | TWI678354B (en) |
| WO (1) | WO2015184229A1 (en) |
| ZA (1) | ZA201607811B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI678354B (en) * | 2014-05-29 | 2019-12-01 | 新加坡商艾佛艾姆希農業新加坡有限公司 | Process to prepare 3-methyl-2-nitrobenzoic acid by air oxidation |
| CN114560773B (en) * | 2022-02-14 | 2023-07-28 | 南昌大学 | Synthesis method of 2-nitro-3-methylbenzoic acid |
| CN114560772B (en) * | 2022-02-14 | 2023-07-28 | 南昌大学 | Synthesis method of 3-methyl-2-nitrobenzoic acid |
| TW202346260A (en) * | 2022-04-14 | 2023-12-01 | 美商富曼西公司 | Methods for the preparation of 5-chloro-2-((ethoxycarbonyl)amino)-3-methylbenzoic acid |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4329518A (en) * | 1979-09-18 | 1982-05-11 | Fmc Corporation | Insecticidal [1,1'-biphenyl]-3-ylmethyl esters |
| JPH05132450A (en) * | 1991-06-21 | 1993-05-28 | Mitsubishi Gas Chem Co Inc | Production of 2-nitro-3-methylbenzoic acid |
| US5591890A (en) * | 1995-11-03 | 1997-01-07 | E. I. Du Pont De Nemours And Company | Process for producing ortho-nitro aromatic acids by oxidation of ortho-nitroalkylaromatic compounds |
| BR9712525A (en) | 1996-10-16 | 1999-10-19 | American Cyanamid Co | The preparation and use of aryl hydroxamic orthosulfonamido acids as matrix metalloproteinase and tace inhibitors |
| JP2000290235A (en) * | 1999-04-07 | 2000-10-17 | Fuso Chemical Co Ltd | Production of 3-nitro-2-methylbenzoic acid |
| JP2001011026A (en) * | 1999-07-02 | 2001-01-16 | Fuso Chemical Co Ltd | Production of 3-methyl-4-nitrobenzoic acid |
| AR036872A1 (en) | 2001-08-13 | 2004-10-13 | Du Pont | ANTRANILAMIDE COMPOSITE, COMPOSITION THAT INCLUDES IT AND METHOD FOR CONTROLLING AN INVERTEBRATE PEST |
| WO2004014873A1 (en) * | 2002-08-09 | 2004-02-19 | Kyorin Pharmaceutical Co., Ltd. | 4-substituted quinazoline-8-carboxyamide derivative and pharmaceutically acceptable addition salt thereof |
| MY140912A (en) | 2004-07-26 | 2010-01-29 | Du Pont | Mixtures of anthranilamide invertebrate pest control agents |
| TWI363756B (en) * | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| WO2006080311A1 (en) * | 2005-01-25 | 2006-08-03 | Ishihara Sangyo Kaisha, Ltd. | Anthranilamide compound, method for producing same and pest control agent containing same |
| JP2006232814A (en) * | 2005-01-25 | 2006-09-07 | Ishihara Sangyo Kaisha Ltd | Anthranilamide-based compound, method for producing the same and pest control agent containing the same |
| JP2009062277A (en) * | 2005-12-27 | 2009-03-26 | Nippon Soda Co Ltd | Benzisothiazoline compound and pest control agent |
| RS53348B (en) | 2006-07-19 | 2014-10-31 | E.I. Du Pont De Nemours And Company | Process for making 3-substituted 2-amino-5-halobenzamides |
| CN100434175C (en) * | 2006-10-17 | 2008-11-19 | 郑州大学 | Catalyst and its use for synthesizing 4-nitro-3-methyl benzoic acid |
| TWI395728B (en) | 2006-12-06 | 2013-05-11 | Du Pont | Process for preparing 2-amino-5-cyanobenzoic acid derivatives |
| TWI415827B (en) | 2006-12-21 | 2013-11-21 | Du Pont | Process for preparing 2-amino-5-cyanobenzoic acid derivatives |
| TWI430980B (en) | 2007-06-29 | 2014-03-21 | Du Pont | Process for preparing 2-amino-5-cyanobenzoic acid derivatives |
| JP5449181B2 (en) | 2007-11-08 | 2014-03-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Process for preparing 2-amino-5-cyanobenzoic acid derivatives |
| TWI432421B (en) * | 2007-12-19 | 2014-04-01 | Du Pont | Process for preparing 2-amino-5-cyanobenzoic acid derivatives |
| TWI431000B (en) * | 2008-03-05 | 2014-03-21 | Du Pont | Process for preparing 2-amino-5-cyanobenzoic acid derivatives |
| DE102010030629A1 (en) | 2010-06-29 | 2011-12-29 | Robert Bosch Gmbh | Speed sensor, vehicle dynamics control device, control device and systems with such devices and method for receiving data via a radio station by the control unit |
| MX2013008560A (en) * | 2011-01-28 | 2013-08-21 | Du Pont | Method for preparing 2-aminobenzamide derivatives. |
| CN103396467B (en) * | 2013-08-05 | 2015-01-28 | 上海杏灵科技药业股份有限公司 | Preparation method of sterol compound |
| TWI678354B (en) * | 2014-05-29 | 2019-12-01 | 新加坡商艾佛艾姆希農業新加坡有限公司 | Process to prepare 3-methyl-2-nitrobenzoic acid by air oxidation |
-
2015
- 2015-05-19 TW TW104115844A patent/TWI678354B/en active
- 2015-05-29 SG SG10201810692VA patent/SG10201810692VA/en unknown
- 2015-05-29 AU AU2015266819A patent/AU2015266819B2/en active Active
- 2015-05-29 US US15/313,365 patent/US9828328B2/en active Active
- 2015-05-29 SG SG11201609547SA patent/SG11201609547SA/en unknown
- 2015-05-29 KR KR1020237011626A patent/KR20230052989A/en not_active Application Discontinuation
- 2015-05-29 CN CN202310119131.0A patent/CN116283596A/en active Pending
- 2015-05-29 EP EP15727281.6A patent/EP3148962B1/en active Active
- 2015-05-29 BR BR112016027556-0A patent/BR112016027556B1/en active IP Right Grant
- 2015-05-29 RU RU2016151919A patent/RU2689126C2/en active
- 2015-05-29 WO PCT/US2015/033131 patent/WO2015184229A1/en active Application Filing
- 2015-05-29 HU HUE15727281A patent/HUE050832T2/en unknown
- 2015-05-29 JP JP2016569944A patent/JP6611735B2/en active Active
- 2015-05-29 CN CN201580028605.4A patent/CN106458843A/en active Pending
- 2015-05-29 MX MX2016015454A patent/MX2016015454A/en unknown
- 2015-05-29 PL PL15727281T patent/PL3148962T3/en unknown
-
2016
- 2016-11-07 IL IL248796A patent/IL248796B/en active IP Right Grant
- 2016-11-11 ZA ZA2016/07811A patent/ZA201607811B/en unknown
-
2017
- 2017-11-21 US US15/819,646 patent/US10155718B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US9828328B2 (en) | 2017-11-28 |
| US10155718B2 (en) | 2018-12-18 |
| BR112016027556A2 (en) | 2017-08-15 |
| CN106458843A (en) | 2017-02-22 |
| WO2015184229A1 (en) | 2015-12-03 |
| JP6611735B2 (en) | 2019-11-27 |
| KR20170013249A (en) | 2017-02-06 |
| PL3148962T3 (en) | 2020-12-28 |
| US20180072653A1 (en) | 2018-03-15 |
| HUE050832T2 (en) | 2021-01-28 |
| JP2017516808A (en) | 2017-06-22 |
| KR20230052989A (en) | 2023-04-20 |
| US20170197907A1 (en) | 2017-07-13 |
| EP3148962A1 (en) | 2017-04-05 |
| BR112016027556B1 (en) | 2021-08-10 |
| TW201602058A (en) | 2016-01-16 |
| MX2016015454A (en) | 2017-03-23 |
| IL248796B (en) | 2020-02-27 |
| RU2689126C2 (en) | 2019-05-24 |
| ZA201607811B (en) | 2018-05-30 |
| SG11201609547SA (en) | 2016-12-29 |
| EP3148962B1 (en) | 2020-05-13 |
| RU2016151919A3 (en) | 2018-12-03 |
| RU2016151919A (en) | 2018-07-02 |
| TWI678354B (en) | 2019-12-01 |
| CN116283596A (en) | 2023-06-23 |
| AU2015266819A1 (en) | 2016-11-24 |
| IL248796A0 (en) | 2017-01-31 |
| AU2015266819B2 (en) | 2019-04-04 |
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