3-(dimethylamino)-N-(3-nitrophenyl)propanamide → N-(3-Aminophenyl)-3-(dimethylamino)propanamide

Participants

Reaction Steps

10% Palladium on charcoal (1.0 g) was suspended in a solution of 3-(dimethylamino)-N-(3-nitrophenyl)propanamide (4.7 g, 20 mmol) in ethyl acetate. The mixture was hydrogenated at 35 psi overnight. The reaction mixture was filtered through a pad of Celite. The filter cake was washed successively with ethyl acetate and methanol. The combined filtrate and washings were evaporated in vacuo to dryness to give N-(3-aminophenyl)-3-(dimethylamino)propanamide as brown gum, 3.9 g (94%). 1H NMR (DMSO-d6) δ: 2.16 (6H, s, CH3), 2.36 (2H, t, J=6.8 Hz, CH2), 3.40 (2H, t, J=6.8 Hz, CH2), 5.20 (2H, brs, NH2), 6.66 (1H, d, J=7.8 Hz, Ar—H), 6.91 (1H, d, J=7.7 Hz, Ar—H), 7.04 (1H, s, Ar—H), 7.15 (1H, t, J=7.4 Hz, Ar—H), 9.05-9.08 (1H, brs, NH).

Provenance & Evidence