Preparation of ortho-methyl anilines from ortho-amino benzyl sulfoxides

Abstract From the Canadian patent

This invention relates, in one of its aspects to a process, for the preparation of ortho-methyl anilines from ortho-amino benzyl sulfoxides. An ortho-amino benzyl sulfoxide is converted to an orthoamino benzyl halide by reaction with a nonoxidizing acid halide and is converted to a stable quaternary salt by reaction with a tertiary amine preferably in the presence of an alcohol. The quaternary salt may be cleaved by hydrogenation to form ortho-methyl anilines. Other aspects of the invention relate to novel intermediate quaternary salts and to a process for forming those quaternary salts.