Organic Chemistry Portal



Methyl Hydrazinocarboxylate as a Practical Alternative to Hydrazine in the Wolff-Kishner Reaction

Philippa B. Cranwell*, Andrew T. Russell*, Christopher D. Smith*

*Department of Chemistry, University of Reading, Whiteknights, Reading, RG6 6AD, UK, Email:,,

P. B. Cranwell, A. T. Russell, C. D. Smith, Synlett, 2016, 27, 131-135.

DOI: 10.1055/s-0035-1560805


A facile protocol for the reduction of aromatic ketones and aldehydes to the corresponding methylene unit involves the synthesis of a carbomethoxyhydrazone intermediate that is easily decomposed to the reduced product. The reaction avoids the use of pernicious hydrazine.

see article for more examples

Key Words

reduction, aldehydes, ketones, heterocycles, hydrazones, hydrazine, alkanes, Wolff-Kishner Reduction

ID: J60-Y2016