A mild chemospecific reductive dehalogenation of ethylaminobenzamides with lithium aluminum hydride

Article abstract of DOI:10.1016/S0040-4039(99)01397-0

A mild reduction of ortho-fluoro benzamides was discovered using LAH. The reaction proceeds cleanly and in moderate yields. The scope of the reaction is explored and a mechanism is proposed. A two carbon spacer between the amide and a 3°amine is optimal for this chelation controlled reaction.