4-(Azidomethyl)benzonitrile → 4-(Aminomethyl)benzonitrile

Participants

Reaction Steps

10% Pd-on-C (Aldrich, 800 mg) catalyst was added to a solution of α-azido-4-cyanotoluene (compound 4-2, 8 g, 51 mmol) in EtOAc (150 ml). The reaction mixture was hydrogenated (H2, 45 psi) in a Parr apparatus for 11 hours. Catalyst was removed by filtering and the solvent was removed under vacuum to give the title compound (6.3 g, 93%). 1H NMR (CDCl3): δ 3.85 (s, 2H), 7.45 (d, 2H, J=8.1), 7.60 (d, 2H, J=8.1 Hz), 7.78 (s, 2H, NH2).

Provenance & Evidence