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

【结构式】

【分子编号】33299

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

【CA登记号】

【分子式】C₁₉H₂₁NO₂

【分子量】295.38128

【元素组成】C 77.26% H 7.17% N 4.74% O 10.83%

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：(VII)

The reaction of (II) with benzaldehyde (VI) in refluxing toluene gives ethyl p-benzylideneamino-alpha-methylphenylacetate (VII), which is reduced with H2 over PtO2 in ethanol to the N-benzyl derivative (VIII). The acylation of (VIII) with phosgene by means of pyridine in toluene yields the N-chlorocarbonyl compound (IX), which is then cyclized to the isoindolinone (IV) with AlCl3 in refluxing 1,2-dichloroethane. Finally, this compound is hydrolyzed with K2CO3 in refluxing ethanol - 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】 Nannini, G.; et al.; New analgesic-antiinflammatory drugs. 1-oxo-2-substituted isoindoline derivatives. Arzneim-Forsch Drug Res 1973, 23, 8, 1090.
【3】 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
(II)	33295	ethyl 2-(4-aminophenyl)butanoate		C₁₂H₁₇NO₂	详情	详情
(IV)	33297	ethyl 2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]butanoate		C₂₀H₂₁NO₃	详情	详情
(VI)	10498	Benzaldehyde;Benzoic aldehyde;Phenylmethanal	100-52-7	C₇H₆O	详情	详情
(VII)	33299	ethyl 2-(4-[[(E)-benzylidene]amino]phenyl)butanoate		C₁₉H₂₁NO₂	详情	详情
(VIII)	33300	ethyl 2-[4-(benzylamino)phenyl]butanoate		C₁₉H₂₃NO₂	详情	详情
(IX)	33301	ethyl 2-[4-[benzyl(chlorocarbonyl)amino]phenyl]butanoate		C₂₀H₂₂ClNO₃	详情	详情

Extended Information