Assessment of a Reductive Amination Route to Methyl(3-nitrobenzyl)amine Hydrochloride

Abstract

During the development of a sodium borohydride mediated reductive amination of 3-nitrobenzaldehyde with methylamine, studies revealed that partial reduction of the nitro group occurred, and potentially dangerous azo- and azoxy-containing products were generated. Borane- tert -butylamine activated with methanesulfonic acid was determined to be a safer reducing agent, and abuse tests on the reduction stage of the process have demonstrated that partial reduction of the nitro group did not occur. Conditions were developed that were suitable for scale-up to a pilot plant.