Chemical Properties of 6-Methyluracil-5-carbaldehyde Oxime

Abstract

Oxidative chlorination of 6-methyluracil-5-carbaldehyde oxime in a two-phase system gave 7V-hydroxy-6-methyluracil-5-carboximidoyl chloride, and its bromination afforded ipso-substitution products, 5-bromo-6-methyluracil and 5,5-dibromo-6-hydroxy-6-methyl-5,6-dihydrouracil. The reaction of the title compound with acetic anhydride led to the formation of 6-methyluracil-5-carbonitrile or O-acetyl derivative, depending on the temperature. 7V-Hydroxy-6-methyluracyl-5-carboximidoyl chloride reacted with acetic acid at 100°C or with potassium iodide in boiling acetone to produce uracil-5-hydroxamic acid which was converted with high yields into the corresponding methyl ester and hydroximic acid amide. Quaternary ammonium salts were obtained by reactions of N-hydroxy-6-methyluracil-5-carboximidoyl chloride with pyridine and 1-methyl-1H-imidazole.