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Synthesis of 14C-labeled aminoglutethimide

✍ Scribed by Naba K. Chaudhuri; Ofelia Servando; Ming-Sang Sung; Heinz Baumann

Publisher: John Wiley and Sons
Year: 1984
Tongue: French
Weight: 367 KB
Volume: 21
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580210302

No coin nor oath required. For personal study only.

✦ Synopsis

A new procedure has been developed for the synthesis of I4C-labeled glutethimide with an improved yield from K14CN. In this procedure benzyl cyanide prepared from benzyl chloride and K14CN was almost quantitatively monoethylated by an ion-pair extraction method using 50% excess of tetrabutylammonium hydroxide as the catalyst. Michael addition of methyl acrylate to monoethylbenzyl cyanide followed by hydrolysis with H2SO4 gave glutethimide which was then nitrated (HNO3 + H2SO4) and catalytically reduced to aminoglutethimide. The best result was obtained when the intermediate =-nitroglutethimide was isolated in pure form by crystallization and then reduced in the presence of 10% Pd/C. When the nitration product (which was a mixture of isomers) was reduced without purification, isolation of pure p-aminoglutethimide was more difficult and the yield was much lower.

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