N-Decyl-3-phenyl-3-(3-nitrophenyl)propenamide → N-Decyl-3-phenyl-3-(3-aminophenyl)propenamide

Participants

Reaction Steps

Reduction of 10.7 g. of N-decyl-3-phenyl-3-(3-nitrophenyl)propenamide with 7.3 g. of iron powder in acetic acid, according to the procedure of Preparation 25, afforded the title compound as an oil. This product was chromatographed on 370 g. of silica gel, eluting with chloroform containing 1% ethanol. This gave 2.2 g. of trans-N-decyl-3-phenyl-3-(3-aminophenyl)propenamide and 0.7 g of cis-N-decyl-3-phenyl-3-(3-aminophenyl)propenamide. The NMR spectrum of the trans-isomer (in CDCl3) showed absorptions at 0.95 (m), 1.25 (s), 3.10 (m), 3.75 (b), 6.35 (s), 6.65 (m) and 7.30 (s) ppm. The NMR spectrum of the cis-isomer (in CDCl3) showed absorptions at 0.90 (m), 1.25 (s), 3.05 (b), 3.65 (b), 5.20 (b), 6.35 (s), 6.65 (m) and 7.15 (m) ppm.

Provenance & Evidence