A. Shinkwin, M. Threadgill
Nov 1, 1996
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Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
Reaction of 3-cyanothiophene with one equivalent of potassium nitrate in concentrated sulphuric acid causes nitration, concurrent with hydrolysis of the nitrile, to give 5-nitrothiophene-3-carboxamide in high yield. Similarly, 2-cyanothiophene gives 4-nitrothiophene-2-carboxamide and 5-nitrothiophene-2-carboxamide, benzonitrile gives 3-nitrobenzamide and 4-methylbenzonitrile gives 4-methyl-3-nitrobenzamide. Extension of this process to use of potassium [ 15 N]-nitrate, formed from [ 15 N]-nitric acid (95% isotopic enrichment), enables preparation of the corresponding [ 15 N]-nitrothiophene-carboxamides in high isotopic yield.