Benzoylhydrazine → HCID 53791839, compound

Participants

Reaction Steps

A solution of 2.2 g (15.9 mmol) of benzoic hydrazide in 50 ml of dry EtOH was stirred under N2 at -10° C. as a solution of 2.5 g (15.1 mmol) of ethyl valerimidate hydrochloride [prepared by method of A. H. Hill and I. Rabinowitz, J. Am. Chem. Soc. 48, 734 (1926)] in 50 ml of dry EtOH was added dropwise over about 15 minutes. Stirring was continued at -10° C. for 3 hours, during which time a white precipitate separated. The cold mixture was filtered through Celite, and the filtrate was co-evaporated with CHCl3 at 10° C. The residue was chromatographed twice on silica gel columns (gradient elution with 0.3-5% MeOH in CH2Cl2) to give 951 mg (25%) of the title compound as a cream-colored semi-solid, suitable for use without further purification (TLC in 97:3 CH2Cl2 -MeOH). 1H NMR (CDCl3, 400 MHz) was complex, suggesting that the product is a mixture of syn- and anti-isomers.

Provenance & Evidence