Preparation of substituted hydrazines
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Abstract
Although a large number of substituted hydrazines are known, the preparation of simple monoalkylhydrazines in a manner suitable for the large-scale economical synthesis has never been developed. Three methods commonly employed in the laboratory i.e. the direct alkylation of hydrazine by an alkyl halide, the alkylation of benzalazine with alkyl sulfates and the catalytic reduction of hydrazones all have serious limitations.
It appears that the reduction of an N-nitro or N-nitroso group should give a hydrazine derivative if the reduction could be carried out under conditions which would reduce these groups without scission of the nitrogen to nitrogen bond. Such reductions of a few compounds, notably N-methyl-N-nitrosourea, have been known for some time but the yields are either low or not given in the literature in most cases.
The current research project was directed toward the development of suitable conditions for this desired reduction without hydrogenolysis of the N-N bond. Many possible reducing agents are known and should be investigated; the present paper deals only with the reduction of these compounds with zinc dust and dilute acetic acid [TRUNCATED]
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Thesis (M.A.)--Boston University
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