Reduction of Amides with NaBH₄ in Diglyme at 162 °C.

Abstract

Amines Amines Q 0120Reduction of Amides with NaBH 4 in Diglyme at 162°C. -Reaction of primary aromatic amides, e.g. (I) and (IV), with NaBH 4 in refluxing diglyme provides access to the corresponding nitriles (II) and (V), respectively. The mechanism of this reaction is studied in detail and a plausible scheme is proposed. In the presence of LiCl, however, the reaction of amides with NaBH 4 affords mainly the amines, but the nitriles as primary products are still present. Secondary aromatic amide (X) reacts only in the presence of LiCl to give the amine (XI). An intermediate is isolated from the reaction of benzylformamide (XII) with NaBH 4 /LiCl, which is characterized as a complex containing diglyme, boron, lithium ions and an imide or amide. -(ZHU, H.-J.; LU, K.-T.; SUN, G.-R.; HE, J.-B.; LI, H.-Q.; PITTMAN, C. U. J.; New J. Chem. 27 (2003) 2, 409-413; Dep. Chem., Miss. State Univ., Mississippi State, MS 39762, USA; Eng.) -Mischke 25-105