Triethylamine → 4-Phenyl-2-pyridinecarbonitrile

Participants

Reaction Steps

A solution of 1.90 g (11.1 mmol) of 4-phenylpyridine-N-oxide (available from Aldrich Chemical Co.), 4.8 ml (35 mmol) of sieve-dried triethylamine and 4.7 ml (35 mmol) trimethylsilylcyanide in 10 ml of sieve-dried acetonitrile was heated to 100° for 24 hours. The reaction mixture was cooled, quenched with 1 ml of H2O then added to 50 ml of H2O and extracted with three-25 ml portions of ethyl acetate. The organic extracts were combined, dried (MgSO4), concentrated in vacuo and purified by flash chromatography (silica gel, 1:4 EtOAc/petroleum ether) to give 2-cyano-4-phenylpyridine as a white solid. Recrystallization (EtOAc/petroleum ether) of the solid afforded 1.65 g (83%) of title nitrile as white crystals, m.p. 97°-98°.

Provenance & Evidence