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【结 构 式】

【分子编号】52658

【品名】2-{2-[[(methyloxy)carbonyl](phenyl)amino]phenyl}acetic acid

【CA登记号】

【 分 子 式 】C16H15NO4

【 分 子 量 】285.29944

【元素组成】C 67.36% H 5.3% N 4.91% O 22.43%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

A new process for the preparation of oxcarbamazepine has been reported: Reaction of 1-phenyl-2,3-dihydro-1H-indol-2-one (I) with NaOH in refluxing THF gives 2-[2-(phenylamino)phenyl]acetic acid (II), which is condensed with dimethyl carbonate (III) by means of butyl lithium in the same solvent to yield 2-[2-[N-(methoxycarbonyl)-N-phenylamino]phenyl]acetic acid (IV). Cyclization of compound (IV) by means of polyphosphoric acid (PPA) at 100 C, followed by treatment of the reaction mixture with hot methanol (65 C) affords 10-methoxy-5H-dibenzo[b,f]azepine-5-carboxylic acid methyl ester (V), which is treated with NaOH in polyethyleneglycol at 100 C to provide 10-methoxy-5H-dibenzo[b,f]azepine (VI). Reaction of (VI) with sodium cyanate in acetic acid gives 10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide (VII), which is finally treated with H2SO4.

1 Kaufmann, D.; Lohse, O.; Zaugg, W.; Funfschilling, P.; Beutler, U. (Novartis AG; Novartis-Erfindungen VmbH); Dibenzo [b,f]azepine derivs. and their preparation. WO 0156992 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 52656 1-phenyl-1,3-dihydro-2H-indol-2-one C14H11NO 详情 详情
(II) 52657 2-[2-(phenylamino)phenyl]acetic acid C14H13NO2 详情 详情
(III) 34197 dimethyl carbonate 616-38-6 C3H6O3 详情 详情
(IV) 52658 2-{2-[[(methyloxy)carbonyl](phenyl)amino]phenyl}acetic acid C16H15NO4 详情 详情
(V) 52659 methyl 10-(methyloxy)-5H-dibenzo[b,f]azepine-5-carboxylate C17H15NO3 详情 详情
(VI) 24333 10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene 4698-11-7 C15H13NO 详情 详情
(VII) 24335 10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide C16H14N2O2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

 

1 Kaufmann D, Fuenfschilling PC,Beutler U, et al.2004.A new synthesis of oxcarbazepine using a friedelcrafts cyclization strategy. Tetrahedron Lett,45:5275-5278.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 52658 2-{2-[[(methyloxy)carbonyl](phenyl)amino]phenyl}acetic acid C16H15NO4 详情 详情
(II) 69515 methyl 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxylate C16H13NO3 详情 详情
(III) 52659 methyl 10-(methyloxy)-5H-dibenzo[b,f]azepine-5-carboxylate C17H15NO3 详情 详情
(IV) 24333 10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene 4698-11-7 C15H13NO 详情 详情
Extended Information