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【结 构 式】 
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【分子编号】33309 【品名】2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]butanenitrile 【CA登记号】 |
【 分 子 式 】C18H16N2O 【 分 子 量 】276.33792 【元素组成】C 78.24% H 5.84% N 10.14% O 5.79% |
合成路线1
该中间体在本合成路线中的序号：(XVIII)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.
| 【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 |