1-phenyl-1,3-dihydro-2H-indol-2-one -Drug Synthesis Database

【结构式】

【分子编号】52656

【品名】1-phenyl-1,3-dihydro-2H-indol-2-one

【CA登记号】

【分子式】C₁₄H₁₁NO

【分子量】209.24748

【元素组成】C 80.36% H 5.3% N 6.69% O 7.65%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

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.

参考文献中间体

合成目标

【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：(VII)

参考文献中间体

合成目标

【1】 Fuenfschilling PC, Zang W, Beutler U et al. 2005.A new Industrial Process for Oxcarbazepine. Org.Proc. Res. Dev.,9:272-277.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	69514	2-(2-(2-methoxy-2-oxo-1-phenylethyl)phenyl)acetic acid	C₁₇H₁₆O₄	详情	详情
(VII)	52656	1-phenyl-1,3-dihydro-2H-indol-2-one	C₁₄H₁₁NO	详情	详情
(VIII)	69516	sodium 2-(2-(phenylamino)phenyl)acetate	C₁₄H₁₂NNaO₂	详情	详情
(IX)	69517	lithium sodium (2-(carboxylatomethyl)phenyl)(phenyl)amide	C₁₄H₁₁LiNNaO₂	详情	详情

Extended Information