JP5449181B2 - ２−アミノ−５−シアノ安息香酸誘導体を調製するための方法 - Google Patents
２−アミノ−５−シアノ安息香酸誘導体を調製するための方法 Download PDFInfo
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- JP5449181B2 JP5449181B2 JP2010533259A JP2010533259A JP5449181B2 JP 5449181 B2 JP5449181 B2 JP 5449181B2 JP 2010533259 A JP2010533259 A JP 2010533259A JP 2010533259 A JP2010533259 A JP 2010533259A JP 5449181 B2 JP5449181 B2 JP 5449181B2
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- HQNZNIJPAYTWJK-UHFFFAOYSA-N 2-amino-5-cyanobenzoic acid Chemical class NC1=CC=C(C#N)C=C1C(O)=O HQNZNIJPAYTWJK-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 327
- 150000001875 compounds Chemical class 0.000 claims abstract description 320
- 239000002904 solvent Substances 0.000 claims abstract description 130
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 93
- 239000003446 ligand Substances 0.000 claims abstract description 55
- 229910052751 metal Inorganic materials 0.000 claims abstract description 42
- 239000002184 metal Substances 0.000 claims abstract description 42
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 33
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 33
- 150000002825 nitriles Chemical class 0.000 claims abstract description 19
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 13
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 13
- 125000006450 cyclopropyl cyclopropyl group Chemical group 0.000 claims abstract description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 12
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims abstract description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 215
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 144
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 53
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
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- 239000011701 zinc Substances 0.000 claims description 43
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- 125000001424 substituent group Chemical group 0.000 claims description 28
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 25
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- 229910052799 carbon Inorganic materials 0.000 claims description 22
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 17
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 14
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- 125000004122 cyclic group Chemical group 0.000 claims description 11
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- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 10
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- 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 description 8
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- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
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- 238000007254 oxidation reaction Methods 0.000 description 12
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- KGZYALLFLANLBU-UHFFFAOYSA-N 2-amino-5-bromo-n,3-dimethylbenzamide Chemical compound CNC(=O)C1=CC(Br)=CC(C)=C1N KGZYALLFLANLBU-UHFFFAOYSA-N 0.000 description 11
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- 229910052760 oxygen Inorganic materials 0.000 description 11
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 10
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- 238000005481 NMR spectroscopy Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
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- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US229907P | 2007-11-08 | 2007-11-08 | |
| US61/002,299 | 2007-11-08 | ||
| PCT/US2008/082739 WO2009061991A1 (en) | 2007-11-08 | 2008-11-07 | Process for preparing 2-amino-5-cyanobenzoic acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011503096A JP2011503096A (ja) | 2011-01-27 |
| JP2011503096A5 JP2011503096A5 (enExample) | 2011-12-22 |
| JP5449181B2 true JP5449181B2 (ja) | 2014-03-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010533259A Expired - Fee Related JP5449181B2 (ja) | 2007-11-08 | 2008-11-07 | ２−アミノ−５−シアノ安息香酸誘導体を調製するための方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8212075B2 (enExample) |
| EP (1) | EP2205555B1 (enExample) |
| JP (1) | JP5449181B2 (enExample) |
| KR (1) | KR20100098382A (enExample) |
| CN (1) | CN101855202B (enExample) |
| AT (1) | ATE538085T1 (enExample) |
| AU (1) | AU2008323843B2 (enExample) |
| BR (1) | BRPI0817168A2 (enExample) |
| IL (1) | IL205378A (enExample) |
| TW (1) | TWI434839B (enExample) |
| WO (1) | WO2009061991A1 (enExample) |
| ZA (1) | ZA201002646B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5926253B2 (ja) | 2010-07-09 | 2016-05-25 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 有害生物駆除剤としてのアントラニルアミド誘導体 |
| TW201247631A (en) | 2011-04-28 | 2012-12-01 | Du Pont | Herbicidal pyrazinones |
| WO2013007603A1 (de) * | 2011-07-08 | 2013-01-17 | Bayer Intellectual Property Gmbh | Verfahren zur herstellung von 2-amino-5-cyano-n,3-dimethylbenzamid |
| CN104245666B (zh) | 2012-02-07 | 2019-01-11 | 拜耳知识产权有限责任公司 | 取代的邻氨基苯甲酸衍生物的制备方法 |
| TWI678354B (zh) | 2014-05-29 | 2019-12-01 | 新加坡商艾佛艾姆希農業新加坡有限公司 | 藉空氣氧化製備３-甲基-２-硝基苯甲酸之製程 |
| CN108623495A (zh) * | 2017-03-15 | 2018-10-09 | 中国科学院上海有机化学研究所 | 一种芳香腈或杂芳香腈类化合物的制备方法 |
| CN110117237B (zh) * | 2018-02-05 | 2024-02-02 | 中国科学院上海有机化学研究所 | 一种芳香腈或烯基腈类化合物的制备方法 |
| CN113692406B (zh) | 2019-02-18 | 2024-07-23 | Pi工业有限公司 | 制备邻甲酰胺基苯甲酰胺类化合物及其中间体的方法 |
| CN113614063A (zh) | 2019-02-22 | 2021-11-05 | Pi工业有限公司 | 合成氨茴二酰胺化合物及其中间体的方法 |
| CN111533649B (zh) * | 2020-06-01 | 2023-03-21 | 南京工业大学 | 一种酸类化合物的合成方法 |
| WO2021249396A1 (en) * | 2020-06-08 | 2021-12-16 | Adama Makhteshim Ltd. | The process of preparation of anthranilamides |
| TW202222162A (zh) | 2020-09-26 | 2022-06-16 | 印度商皮埃企業有限公司 | 鄰胺苯甲酸／醯胺化合物及其中間體的合成方法 |
| US20240308988A1 (en) | 2021-08-05 | 2024-09-19 | Syngenta Crop Protection Ag | Method For Controlling Diamide Resistant Pests and Compounds Therefor |
| CN114011470A (zh) * | 2021-11-29 | 2022-02-08 | 首都师范大学 | 一种用于水解三磷酸腺苷的催化剂及其制备方法和应用 |
| WO2026047667A1 (en) * | 2024-08-26 | 2026-03-05 | Adama Makhteshim Ltd. | Process for preparing amino-cyano-benzene derivatives |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2010159A1 (en) * | 1989-02-21 | 1990-08-21 | James J. Maul | Cyanation of haloaromatics utilizing catalysts generated in situ starting with nic1 or nic1 6h 0 |
| EP0613719A1 (en) * | 1993-03-05 | 1994-09-07 | Duphar International Research B.V | Nickel catalyst for the cyanation of aromatic halides |
| MY142967A (en) | 2001-08-13 | 2011-01-31 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
| WO2004067528A1 (en) | 2003-01-28 | 2004-08-12 | E.I. Du Pont De Nemours And Company | Cyano anthranilamide insecticides |
| MY140912A (en) | 2004-07-26 | 2010-01-29 | Du Pont | Mixtures of anthranilamide invertebrate pest control agents |
| JP5215669B2 (ja) | 2004-11-18 | 2013-06-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | アントラニルアミド殺虫剤 |
| TWI363756B (en) * | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| TWI430980B (zh) * | 2007-06-29 | 2014-03-21 | Du Pont | 製備２－胺基－5－氰基苯甲酸衍生物之方法 |
-
2008
- 2008-11-07 JP JP2010533259A patent/JP5449181B2/ja not_active Expired - Fee Related
- 2008-11-07 US US12/741,635 patent/US8212075B2/en active Active
- 2008-11-07 EP EP08847056A patent/EP2205555B1/en not_active Not-in-force
- 2008-11-07 CN CN200880115133.6A patent/CN101855202B/zh active Active
- 2008-11-07 AU AU2008323843A patent/AU2008323843B2/en not_active Ceased
- 2008-11-07 KR KR1020107012505A patent/KR20100098382A/ko not_active Ceased
- 2008-11-07 WO PCT/US2008/082739 patent/WO2009061991A1/en not_active Ceased
- 2008-11-07 BR BRPI0817168 patent/BRPI0817168A2/pt not_active IP Right Cessation
- 2008-11-07 AT AT08847056T patent/ATE538085T1/de active
- 2008-11-07 TW TW097143244A patent/TWI434839B/zh not_active IP Right Cessation
-
2010
- 2010-04-15 ZA ZA2010/02646A patent/ZA201002646B/en unknown
- 2010-04-27 IL IL205378A patent/IL205378A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN101855202B (zh) | 2014-06-25 |
| TW200925157A (en) | 2009-06-16 |
| AU2008323843A1 (en) | 2009-05-14 |
| EP2205555A1 (en) | 2010-07-14 |
| IL205378A (en) | 2013-03-24 |
| US20110034695A1 (en) | 2011-02-10 |
| US8212075B2 (en) | 2012-07-03 |
| WO2009061991A1 (en) | 2009-05-14 |
| EP2205555B1 (en) | 2011-12-21 |
| BRPI0817168A2 (pt) | 2015-03-31 |
| ZA201002646B (en) | 2011-06-29 |
| AU2008323843B2 (en) | 2013-05-16 |
| IL205378A0 (en) | 2010-12-30 |
| CN101855202A (zh) | 2010-10-06 |
| JP2011503096A (ja) | 2011-01-27 |
| TWI434839B (zh) | 2014-04-21 |
| ATE538085T1 (de) | 2012-01-15 |
| KR20100098382A (ko) | 2010-09-06 |
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