2-(4-Nitrophenyl)propanenitrile → 4-(1-Aminopropan-2-yl)aniline

Participants

Reaction Steps

2-(4-Nitrophenyl)propionitrile (5.0 g, 28.38 mmoL) was dissolved in a 20% NH3/methanol mixture (100 mL) and treated with Raney Nickel (24.79 g). It was then hydrogenated at 60 psi at room temperature for 4 hr. The reaction was then filtered through a nylon membrane. The filtrate was then concentrated in vacuo to give 4.26 g (100%) of the title compound. It was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 7.00 (d, J=8.46 Hz, 2H) 6.66 (d, J=8.09 Hz, 2H) 3.58 (s, 2H) 2.71-2.85 (m, 2H) 2.56-2.70 (m, 1H) 1.20 (d, J=6.62 Hz, 3H). MS m/z (DCI) 151.0 (M+H)+.

Provenance & Evidence