A New Procedure for Preparation of Carboxylic Acid Hydrazides

The standard method for preparing carboxylic acid hydrazides is hydrazinolysis of esters in alcoholic solutions. However, when applied to α,β-unsaturated esters, the main product typically is the pyrazolidinone resulting from an undesired Michael-type cyclization. Other alternative methodologies rep...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-12, Vol.67 (26), p.9471-9474
Main Authors: Zhang, Xini, Breslav, Michael, Grimm, Jeffrey, Guan, Kailin, Huang, Aihua, Liu, Fuqiang, Maryanoff, Cynthia A, Palmer, David, Patel, Mitul, Qian, Yun, Shaw, Charles, Sorgi, Kirk, Stefanick, Stephen, Xu, Dawei
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:The standard method for preparing carboxylic acid hydrazides is hydrazinolysis of esters in alcoholic solutions. However, when applied to α,β-unsaturated esters, the main product typically is the pyrazolidinone resulting from an undesired Michael-type cyclization. Other alternative methodologies reported for direct preparation of hydrazides from acids are inefficient. We developed an efficient and general process, involving preforming activated esters and/or amides followed by reaction with hydrazine, for the preparation of hydrazides including those of α,β-unsaturated acids. This process gives the desired hydrazides in excellent yield and purity under mild conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo026288n