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【结 构 式】

【分子编号】34093

【品名】6-chloro-2-hydrazino-4-phenylquinoline

【CA登记号】

【 分 子 式 】C15H12ClN3

【 分 子 量 】269.7332

【元素组成】C 66.79% H 4.48% Cl 13.14% N 15.58%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

The reaction of 2,6-dichloro-4-phenylquinoline (I) with refluxing hydrazine hydrate gives 6-chloro-2-hydrazino-4-phenylquinoline (II), which is cyclocondensed with triethyl orthoacetate (A) in refluxing xylene yielding 7-chloro-1-methyl-5-phenyl-s-triazolo[4,3-a]quinoline (III). The oxidation of (III) to 5-chloro-2-(3-methyl-4H-1,2,4-triazol-4-yl)benzophenone (V) can be performed with sodium periodate and ruthenium dioxide in acetone-water, or first with ozone in CH2Cl2 giving 4-(2-benzoyl-4-chlorophenyl)-5-methyl-4H-1,2,4-triazol-3-carboxaldehyde (IV), which is then oxidized to (V) with silver oxide in methanol. The condensation of (V) with formaldehyde in xylene at 125 C affords 5-chloro-2-(3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4-yl)benzophenon (VI), which by reaction with PBr3 in chloroform is converted into 5-chloro-2-(3-bromoethyl-5-methyl-4H-1,2,4-triazol-4-yl)benzophenon (VII). Finally, this product is cyclized with ammonia in THF - methanol.

1 Hester, J.B. Jr.; Process for the production of triazolobenzodiazepines and intermediates. DE 2203782; FR 2124559; GB 1374822; GB 1374823; GB 1374824; GB 1374825; JP 49066679; US 3709898 .
2 Castaner, J.; Chatterjee, S.S.; Alprazolam. Drugs Fut 1976, 1, 12, 551.
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) 12940 1,1-Diethoxyethyl ethyl ether; 1,1,1-Triethoxyethane; Triethyl orthoacetate 78-39-7 C8H18O3 详情 详情
(I) 34092 2,6-dichloro-4-phenylquinoline C15H9Cl2N 详情 详情
(II) 34093 6-chloro-2-hydrazino-4-phenylquinoline C15H12ClN3 详情 详情
(III) 34094 7-chloro-1-methyl-5-phenyl[1,2,4]triazolo[4,3-a]quinoline C17H12ClN3 详情 详情
(IV) 34095 4-(2-benzoyl-4-chlorophenyl)-5-methyl-4H-1,2,4-triazole-3-carbaldehyde C17H12ClN3O2 详情 详情
(V) 34096 [5-chloro-2-(3-methyl-4H-1,2,4-triazol-4-yl)phenyl](phenyl)methanone C16H12ClN3O 详情 详情
(VI) 34097 [5-chloro-2-[3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4-yl]phenyl](phenyl)methanone C17H14ClN3O2 详情 详情
(VII) 34098 [2-[3-(bromomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-5-chlorophenyl](phenyl)methanone C17H13BrClN3O 详情 详情
Extended Information