2-(4-[[(E)-benzylidene]amino]phenyl)butanenitrile -Drug Synthesis Database

【结构式】

【分子编号】33306

【品名】2-(4-[[(E)-benzylidene]amino]phenyl)butanenitrile

【CA登记号】

【分子式】C₁₇H₁₆N₂

【分子量】248.32752

【元素组成】C 82.22% H 6.49% N 11.28%

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：(XV)

The reaction of benzaldehyde (VI) with p-amino-alpha-ethylphenylacetonitrile (XIV) in refluxing toluene gives p-benzylideneamino-alpha-ethylphenylacetonitrile (XV), which is reduced with H2 over PtO2 in ethanol yielding p-benzylamino-alpha-ethylphenylacetonitrile (XVI). The acylation of (XVI) with phosgene by means of pyridine in toluene affords the N-chlorocarbo-nyl compound (XVII), which is cyclized with AlCl3 in refluxing 1,2-dichloroethane to yield 1-oxo-2-[p-(alpha-ethyl-cyanomethyl)phenyl]isoindoline (XVIII). Finally, this compound is hydrolyzed with H2SO4 in refluxing water.

参考文献中间体

合成目标

【1】 Giraldi, P.N.; et al.; Verfahren zur Herstellung von Isoindolinderivaten. AT 325604B; CA 994785; CH 581106; JP 48057965; NL 7215830 .
【2】 de Angelis, L.; Castaner, J.; Indobufen. Drugs Fut 1979, 4, 2, 109.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	10498	Benzaldehyde;Benzoic aldehyde;Phenylmethanal	100-52-7	C₇H₆O	详情	详情
(XIV)	33305	2-(4-aminophenyl)butanenitrile		C₁₀H₁₂N₂	详情	详情
(XV)	33306	2-(4-[[(E)-benzylidene]amino]phenyl)butanenitrile		C₁₇H₁₆N₂	详情	详情
(XVI)	33307	2-[4-(benzylamino)phenyl]butanenitrile		C₁₇H₁₈N₂	详情	详情
(XVII)	33308	1-[benzyl(chlorocarbonyl)amino]-4-(1-cyanopropyl)benzene		C₁₈H₁₇ClN₂O	详情	详情
(XVIII)	33309	2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]butanenitrile		C₁₈H₁₆N₂O	详情	详情

Extended Information