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Synthesis 2009(18): 3174-3176  
DOI: 10.1055/s-0029-1216932
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© Georg Thieme Verlag Stuttgart ˙ New York

A Large-Scale Low-Cost Preparation of N-Benzylhydroxylamine Hydrochloride

Thanh Binh Nguyen, Arnaud Martel, Robert Dhal, Gilles Dujardin*
Laboratoire de Synthèse Organique, UCO2M, UMR 6011 CNRS, Université du Maine, 72085 Le Mans, France
e-Mail: gilles.dujardin@univ-lemans.fr ;
Further Information

Publication History

Received 22 April 2009
Publication Date:
14 August 2009 (online)

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Abstract

A high-yielding, practical two-step procedure for the preparation of N-benzylhydroxylamine starting from dibenzylamine is described­. As specified in the detailed protocol, the reaction can be conveniently carried out on a > 0.5 mol laboratory scale.

Key words

N-benzylhydroxylamine - N-benzylnitrones - 1,3-dipolar cycloaddition - secondary amine oxidation - nitrone hydrolysis

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12

The cost of the tungstate catalyst, used at a 2 mol%, is approximately 60 ı/mol.

13

Evaporation of the solvent (MeOH) at reduced pressure in the presence of large quantities of aqueous H2O2, as described in reference 7.