2-Naphthalenecarbonitrile → 1-(2-Naphthyl)methanamine

Participants

Reaction Steps

A mixture of 10.0 g (65.3 mmole) 2-cyanonaphthalene, 2.0 g Raney Nickel, 100 ml ethanol and 9 ml concentrated ammonium hydroxide was hydrogenated at 36 psi (2.53 kg/cm2) for 4.5 days. The mixture was filtered and the filtrate concentrated in vacuo to an oil. The oil was distilled in vacuo to obtain the desired amine as a colorless liquid which solidified on standing. Yield 2.02 g. TLC on silica gel plates showed one spot at Rf 0.1 upon development with 19:1 chloroform/methanol.

Provenance & Evidence