Methyl 2-Nitrosobenzoate: A Simple Dehydrating Agent for the Synthesis of Nitriles from Aldoximes

A simple and convenient synthesis of nitriles from the corresponding aldoximes using methyl 2-nitrosobenzoate under milder condition has been developed. The reaction proceeds under weak alkaline conditions and, allows for the conversion of a wide variety of aldoximes including aromatic aldoximes, and heterocyclic aldoximes in good to excellent yields in short time. Notably, alpha, beta-unsaturated aldoximes were also compatible with the reaction conditions without any cis/trans isomerization of the double bonds. An unprotected hydroxyl and amine group has no effect on the reaction outcome.