Nitrostyrene to phenetylamine, NaBH4/RaneyNi/N2H4
(Rated as: excellent)
A nitrostyrene is reduced with sodium borohydride in methanol to the phenylnitroethane in 53% yield, followed by catalytic transfer hydrogenation using Raney Nickel and hydrazine hydrate to give the phenethylamine in 83% yield.
To a solution of 1.6g in 40ml methanol was added 1.6g Raney Nickel and 1.6ml hydrazine hydrate and the mixture shaken at ambient temperature for one hour. The resulting mixture on usual workup gave the title amine as an oil (1.2g, 83%). Oxalate salt mp 189-190°C.
Reference: Indian Journal of Chemistry, Vol 22B, 5-8 (1983)