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【结 构 式】 
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【分子编号】24319 【品名】4-chloro-N-(4-methoxyphenyl)benzohydrazide 【CA登记号】 |
【 分 子 式 】C14H13ClN2O2 【 分 子 量 】276.7222 【元素组成】C 60.77% H 4.74% Cl 12.81% N 10.12% O 11.56% |
合成路线1
该中间体在本合成路线中的序号：(I)1) The reaction of N1-(4-chlorobenzoyl)-N1-(4-methoxyphenyl)hydrazine (I) [the starting material for the synthesis of indomethacin], with d,l-(2-carboxyethyl-2-phenyl)-4-oxopentanoate (II) under the conditions of Fischer indole synthesis by means of 100% phosphoric acid in toluene at 100 C. d,l-(2-Carboxyethyl-2-phenyl)-4-oxopentanoate (II) is obtained hy treatment of d,l-tropic acid with levulinic acid chloride.
| 【1】 Grimova, J.; Rabek, V.; Roubal, Z.; Fisnerova, L.; Pharmacologically interesting derivatives of indomethacin. Cesk Farm 1977, 26, 277. |
| 【2】 Fisnerova, L.; Nemecek, O.; Method of producing 2-phenyl-2-carboxyethyl ester of 1-p-chlorobenzoyl-5-methoxy-2-methyl-3-indolyl acetic acid. CS 194284 . |
| 【3】 Sletzinger, M.; Chemerda, J.M.; Summit, G.G. (Merck & Co., Inc.); N-acyl-phenylhydrazine sulfamic acids and salts thereof. DE 1643462; DE 1643463; DE 1768016; DE 1770022; FR 1540724; FR 1540725; GB 1161270; GB 1173986 . |
| 【4】 Fisnerova, L.; Nemecek, O.; Method of producing 2-phenyl-2-carboxyethyl ester of levulinic acid. CS 194283 . |
| 【5】 Nemecek, O.; Fisnerova, L.; Grimova, J.; Roubal, Z. (SPOFA - United Pharmaceutical Works); 2-Phenyl-2-carboxyethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate and process for preparation thereof. US 4136194 . |
| 【6】 Fisnerova, L.; Tropesin. Drugs Fut 1986, 11, 9, 779. |
合成路线2
该中间体在本合成路线中的序号：(III)1) By condensation of 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid (II) with benzyl bromoacetate (A) by means of K2CO3 in DMF. 2) By cyclocondensation of a mixture of N-(p-methoxyphenyl)-N-(p-chlorobenzoyl)hydrazine (III) and benzyl levulinate (IV) at 80 C in acetic acid.
| 【1】 Boltze, K.; Brendler, O.; Dell, H.-D.; Jacobi, H.; Novel substituted indole compound, process for the preparation and therapeutic compositions containing it.. DE 2234651; ES 416877; FR 2192828; JP 49043970; US 3910952 . |
| 【2】 Leeson, P.A.; Castaner, J.; Acemetacin. Drugs Fut 1977, 2, 7, 423. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 12869 | benzyl 2-bromoacetate | 5437-45-6 | C9H9BrO2 | 详情 | 详情 |
| (I) | 33962 | 2-(benzyloxy)-2-oxoethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate | C28H24ClNO6 | 详情 | 详情 | |
| (II) | 22930 | 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid | C19H16ClNO4 | 详情 | 详情 | |
| (III) | 24319 | 4-chloro-N-(4-methoxyphenyl)benzohydrazide | C14H13ClN2O2 | 详情 | 详情 | |
| (IV) | 33963 | 2-(benzyloxy)-2-oxoethyl 4-oxopentanoate | C14H16O5 | 详情 | 详情 |