OA11861A - Method for making 2-(N-phenylamino) benzoic acids. - Google Patents
Method for making 2-(N-phenylamino) benzoic acids. Download PDFInfo
- Publication number
- OA11861A OA11861A OA1200100260A OA1200100260A OA11861A OA 11861 A OA11861 A OA 11861A OA 1200100260 A OA1200100260 A OA 1200100260A OA 1200100260 A OA1200100260 A OA 1200100260A OA 11861 A OA11861 A OA 11861A
- Authority
- OA
- OAPI
- Prior art keywords
- benzoic acid
- phenylamino
- aniline
- hexamethyldisilazide
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 39
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 title claims abstract description 17
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 50
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 26
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 25
- XGIUDIMNNMKGDE-UHFFFAOYSA-N bis(trimethylsilyl)azanide Chemical compound C[Si](C)(C)[N-][Si](C)(C)C XGIUDIMNNMKGDE-UHFFFAOYSA-N 0.000 claims abstract description 11
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- MYDAOWXYGPEPJT-UHFFFAOYSA-N 2-chloro-4-iodoaniline Chemical group NC1=CC=C(I)C=C1Cl MYDAOWXYGPEPJT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 abstract description 7
- 230000008878 coupling Effects 0.000 abstract description 4
- 238000010168 coupling process Methods 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract 1
- 229960004365 benzoic acid Drugs 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical class C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WEPXLRANFJEOFZ-UHFFFAOYSA-N 2,3,4-trifluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(F)=C1F WEPXLRANFJEOFZ-UHFFFAOYSA-N 0.000 description 1
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 1
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 1
- BGKLFAQCHHCZRZ-UHFFFAOYSA-N 4-iodo-2-methylaniline Chemical compound CC1=CC(I)=CC=C1N BGKLFAQCHHCZRZ-UHFFFAOYSA-N 0.000 description 1
- 239000012820 MEK1 Inhibitor Substances 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 208000037803 restenosis Diseases 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13038499P | 1999-04-21 | 1999-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11861A true OA11861A (en) | 2006-03-02 |
Family
ID=22444462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200100260A OA11861A (en) | 1999-04-21 | 2000-02-16 | Method for making 2-(N-phenylamino) benzoic acids. |
Country Status (34)
| Country | Link |
|---|---|
| EP (1) | EP1171418B1 (pt) |
| JP (1) | JP3769192B2 (pt) |
| KR (1) | KR20010108521A (pt) |
| CN (1) | CN1213997C (pt) |
| AP (1) | AP2001002328A0 (pt) |
| AT (1) | ATE286015T1 (pt) |
| AU (1) | AU773096B2 (pt) |
| BG (1) | BG106132A (pt) |
| BR (1) | BR0009886A (pt) |
| CA (1) | CA2368807A1 (pt) |
| CR (1) | CR6486A (pt) |
| CU (1) | CU22996A3 (pt) |
| DE (1) | DE60017109T2 (pt) |
| DK (1) | DK1171418T3 (pt) |
| EA (1) | EA004209B1 (pt) |
| EE (1) | EE200100546A (pt) |
| ES (1) | ES2235843T3 (pt) |
| GE (1) | GEP20033089B (pt) |
| HK (1) | HK1045682B (pt) |
| HR (1) | HRP20010850A2 (pt) |
| HU (1) | HUP0200932A3 (pt) |
| IL (1) | IL146056A0 (pt) |
| MA (1) | MA25412A1 (pt) |
| NO (1) | NO20015095D0 (pt) |
| NZ (1) | NZ515120A (pt) |
| OA (1) | OA11861A (pt) |
| PL (1) | PL351085A1 (pt) |
| PT (1) | PT1171418E (pt) |
| SK (1) | SK14732001A3 (pt) |
| TR (1) | TR200103015T2 (pt) |
| UA (1) | UA70995C2 (pt) |
| WO (1) | WO2000064856A1 (pt) |
| YU (1) | YU73701A (pt) |
| ZA (1) | ZA200107834B (pt) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0113520A (pt) * | 2000-08-25 | 2003-06-24 | Warner Lambert Co | Processo de preparação de ácidos n-aril-antranìlicos e seus derivados |
| JP5025466B2 (ja) * | 2005-04-06 | 2012-09-12 | 中外製薬株式会社 | ２，３，４−トリフルオロ−５−（ヨード又はブロモ）安息香酸の製造方法 |
| JPWO2007021001A1 (ja) * | 2005-08-18 | 2009-02-26 | 宇部興産株式会社 | ２，３，４−トリフルオロ−５−置換安息香酸化合物及びその製法 |
| CA2789373A1 (en) * | 2010-02-19 | 2011-08-25 | Centre National De La Recherche Scientifique | Process for preparing chemical compounds of interest by nucleophilic aromatic substitution of aromatic carboxylic acid derivatives supporting at least one electro-attractive group |
| EP2536683A1 (fr) * | 2010-02-19 | 2012-12-26 | Centre National De La Recherche Scientifique | Procédé de préparation de composés chimiques d'intérêt par substitution nucléophile aromatique |
| JP2016034900A (ja) * | 2012-11-26 | 2016-03-17 | 中外製薬株式会社 | ５−置換−２−フェニルアミノ−ベンズアミド類の製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9810366A (pt) * | 1997-07-01 | 2000-08-29 | Warner Lambert Co | Derivados de ácido 4-bromo ou 4-iodo fenilamino benzidroxîmico e seu uso como inibidores de mek |
-
2000
- 2000-02-16 GE GEAP20006152A patent/GEP20033089B/en unknown
- 2000-02-16 EP EP00913489A patent/EP1171418B1/en not_active Expired - Lifetime
- 2000-02-16 NZ NZ515120A patent/NZ515120A/en unknown
- 2000-02-16 SK SK1473-2001A patent/SK14732001A3/sk unknown
- 2000-02-16 AU AU34928/00A patent/AU773096B2/en not_active Ceased
- 2000-02-16 EE EEP200100546A patent/EE200100546A/xx unknown
- 2000-02-16 CA CA002368807A patent/CA2368807A1/en not_active Abandoned
- 2000-02-16 AT AT00913489T patent/ATE286015T1/de not_active IP Right Cessation
- 2000-02-16 BR BR0009886-8A patent/BR0009886A/pt not_active IP Right Cessation
- 2000-02-16 PT PT00913489T patent/PT1171418E/pt unknown
- 2000-02-16 CN CNB008064423A patent/CN1213997C/zh not_active Expired - Fee Related
- 2000-02-16 HU HU0200932A patent/HUP0200932A3/hu unknown
- 2000-02-16 PL PL00351085A patent/PL351085A1/xx not_active IP Right Cessation
- 2000-02-16 AP APAP/P/2001/002328A patent/AP2001002328A0/en unknown
- 2000-02-16 DE DE60017109T patent/DE60017109T2/de not_active Expired - Fee Related
- 2000-02-16 TR TR2001/03015T patent/TR200103015T2/xx unknown
- 2000-02-16 EA EA200101113A patent/EA004209B1/ru not_active IP Right Cessation
- 2000-02-16 JP JP2000613809A patent/JP3769192B2/ja not_active Expired - Fee Related
- 2000-02-16 IL IL14605600A patent/IL146056A0/xx unknown
- 2000-02-16 UA UA2001096639A patent/UA70995C2/uk unknown
- 2000-02-16 DK DK00913489T patent/DK1171418T3/da active
- 2000-02-16 ES ES00913489T patent/ES2235843T3/es not_active Expired - Lifetime
- 2000-02-16 WO PCT/US2000/003982 patent/WO2000064856A1/en not_active Application Discontinuation
- 2000-02-16 OA OA1200100260A patent/OA11861A/en unknown
- 2000-02-16 KR KR1020017013402A patent/KR20010108521A/ko not_active Application Discontinuation
- 2000-02-16 YU YU73701A patent/YU73701A/sh unknown
-
2001
- 2001-09-21 CU CU20010213A patent/CU22996A3/es unknown
- 2001-09-21 ZA ZA200107834A patent/ZA200107834B/en unknown
- 2001-10-19 NO NO20015095A patent/NO20015095D0/no not_active Application Discontinuation
- 2001-10-19 CR CR6486A patent/CR6486A/es not_active Application Discontinuation
- 2001-11-16 MA MA26413A patent/MA25412A1/fr unknown
- 2001-11-16 HR HR20010850A patent/HRP20010850A2/hr not_active Application Discontinuation
- 2001-11-21 BG BG106132A patent/BG106132A/xx unknown
-
2002
- 2002-09-26 HK HK02107069.9A patent/HK1045682B/zh not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2470015C2 (ru) | Способ получения производных 3-дигалогенметил-пиразол-4-карбоновой кислоты | |
| JP2021529822A (ja) | Ｃ−ｈ酸性（メタ）アクリレートの製造方法 | |
| OA11861A (en) | Method for making 2-(N-phenylamino) benzoic acids. | |
| BR112016010413B1 (pt) | processo para preparação de derivados de 3,5-bis(haloalquil)pirazole a partir de a,a-dihaloaminas | |
| HU204512B (en) | New process for producing quinoline-carboxylic acid derivatives | |
| JP2021506872A (ja) | イミニウム化合物の製造のための方法、及びピラゾール誘導体の製造におけるそれらの適用 | |
| CA2871694A1 (en) | Manufacture of 1-substituted methylidene compounds | |
| JP3002791B2 (ja) | ベンジルフェニルケトン誘導体 | |
| US6686499B1 (en) | Method for making 2-(N-phenylamino)benzoic acids | |
| MXPA01009553A (en) | Method for making 2-(n-phenylamino)benzoic acids | |
| JPH0841030A (ja) | １−（ヘテロ）アリール−３−ヒドロキシピラゾールの製造方法 | |
| HU203539B (en) | Process for producing substituted pyrazol derivatives | |
| JPS61189271A (ja) | １−メチル−５−ヒドロキシピラゾ−ルの製法 | |
| US6570015B2 (en) | Process for producing 2-substituted thiopyrimidine-4-carboxylate | |
| JPH02306950A (ja) | アミノアセタール誘導体 | |
| JPH06157418A (ja) | 還元的脱ハロゲン化法 | |
| JPH01242560A (ja) | ｏ−アミノフエノール類の製造方法 | |
| US4245108A (en) | Process for preparing 2-thio-2-substituted-alkanoic acid derivatives | |
| US2425276A (en) | Aliphatic nitro derivatives of ketoesters and method for preparing them | |
| JP5969958B2 (ja) | 光学活性含フッ素アミノ酸類の製造方法 | |
| JPH11228485A (ja) | ３，３−ジメチル酪酸の製造方法 | |
| EP1436263A4 (en) | METHOD FOR PRODUCING A BETA-KETOESTER COMPOUND | |
| US2460224A (en) | Biotin intermediate | |
| JPS5815948A (ja) | ヒドラジジン類の製造方法 | |
| JPH1171325A (ja) | ４−アリールブタン酸アルキルエステル類の製造方法 |