Convenient Method for Reduction of C-N Double Bonds in Oximes, Imines, and Hydrazones Using Sodium Borohydride–Raney Ni System

Abstract

A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs.

GRAPHICAL ABSTRACT

Keywords:

• C-N double bond
• Raney Ni
• reduction
• sodium borohydride

ACKNOWLEDGMENTS

This work is supported by the National Natural Science Foundation of China (Grant Nos. 30472074 and 30873139) and the Natural Science Foundation of Hebei Province (Nos. B2006000302 and 10276406D6).

Notes

^a All products were characterized by ¹H NMR and their physical properties were compared with the reported values.

^b Isolated yield. The figure in brackets is the yield without Raney Ni.

^a All products were characterized by ¹H NMR, and their physical properties were compared with the reported values.

^b Isolated yield.