The formation of nitriles by pyrolysis of N-substituted chloroacetamides

Abstract

Pyrolysis of chloroacetamides RNHCOCH₂Cl at 780-850°C/0.1-0.4 mm with short contact time gives nitriles RCN in 45-60% yield (R = phenyl, o- tolyl, p-tolyl, benzyl, or cyclohexyl). A mechanism is proposed involving the formation of the iso-nitrile RNC, formaldehyde, and hydrogen chloride. N-Chloroacetylbiphenyl-2-amine gives biphenyl-2- carbonitrile (45%) and phenanthridine (15%).