Chemistry of Diborane and Sodium Borohydride. VI. The Reaction of Amides with Sodium Borohydride

Abstract

The reactions of primary, secondary and tertiary amides with sodium borohydride in refluxing pyridine were examined. Tertiary amides were reduced to the corresponding amines in moderate yield, in case of secondary amide no reaction occured and the starting amide was recovered, primary amides, on the contrary, were dehydrated to nitriles. Especially, when nicotinamide was used, the reduction of pyridine nucleus accompanied by dehydration occured to give 1, 4, 5, 6-tetrahydronicotinonitrile.