Journal of the American Chemical Society 2008-05-07

A new method for N-N bond cleavage of N,N-disubstituted hydrazines to secondary amines and direct ortho amination of naphthol and its analogues.

Qiang Tang, Chao Zhang, Meiming Luo

Index: J. Am. Chem. Soc. 130(18) , 5840-1, (2008)

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Abstract

An unexpected reaction of N,N-disubstituted hydrazine with naphthol and its analogues under simply thermal conditions has been disclosed. 2-Naphthol reacted with various N,N-disubstituted hydrazines under argon to afford 1-amino-2-naphthol and the corresponding secondary amines in excellent yields. Ortho amination of 2-naphthols, hydroxyquinoline, and naphthalenamine occurred when they reacted with N-methyl-N-phenylhydrazine.