✦ LIBER ✦

Transformation of 4-(1-dimethylaminoethylidene)-2-phenyl-5(4H)-oxazolone into methyl 2-benzoylamino-3-oxobutanoate. The synthesis of 1-substituted 4-benzoylamino-3-methyl-5(2H)-pyrazolones

✍ Scribed by UrŠKa Bratušek; AleŠ Hvala; Branko Stanovnik

Publisher: Journal of Heterocyclic Chemistry
Year: 1998
Tongue: English
Weight: 352 KB
Volume: 35
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570350607

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✦ Synopsis

Abstract

Methyl 2‐benzoylamino‐3‐oxobutanoate (3) was prepared from hippuric acid (1) which was converted with N,N‐dimethylacetamide and phosphorus oxychloride into 4‐(1‐dimethylaminoethylidene)‐2‐phenyl‐5(4__H)‐oxazolone (2) followed by hydrolysis with hydrochloric acid in methanol. Compound 3 was treated with hydrazines 4 to give 4‐benzoylamino‐3‐methyl‐1__H‐pyrazol‐5(2__H__)‐one (6a) and its 1‐substituted derivatives 6b‐j. The corresponding hydrazones 5f, i, j were isolated as intermediates.

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