N-(1-Methyldecyl)-3-phenyl-3-(3-nitrophenyl)propenamide → N-(1-Methyldecyl)-3-phenyl-3-(3-aminophenyl)propenamide

Participants

Reaction Steps

Reduction of 11.6 g. of N-(1-methyldecyl)-3-phenyl-3-(3-nitrophenyl)propenamide with 7.7 g. of iron powder in glacial acetic acid, according to the procedure of Preparation 25, afforded the title compound as an oil. This product was chromatographed on 350 g. of silica gel, eluting with chloroform containing 1% ethanol. This gave 2.3 g. of trans-N-(1-methyldecyl)-3-phenyl-3-(3-aminophenyl)propenamide, 0.25 g. of cis-N-(1-methyldecyl)-3-phenyl-3-(3-aminophenyl)propenamide and 6.2 g. of a mixture of these two isomers. Rechromatography of the mixture afforded a further 0.6 g. of the cis-isomer. The NMR spectrum of the trans-isomer (in CDCl3) showed absorptions at 0.85 (m), 1.25 (s), 3.60 (b), 5.15 (b), 6.35 (s), 6.65 (m) and 7.30 (s) ppm.

Provenance & Evidence