Nitric Acid → 3-Methyl-5-nitro-2-pyridone

A solution of (3-methylpyridin-2-yl)amine (10 g, 90 mmol) in 50 ml of concentrated sulfuric acid was cooled to 5° C. in ice-salt bath. A mixture of 7 ml each of concentrated sulfuric acid and concentrated nitric acid was added slowly with stirring while maintaining the reaction temperature below 10° C. This mixture was then allowed to warm to 30° C. overnight. The solution was stirred rapidly while 7 ml of concentrated nitric acid was added at such a rate as to keep the temperature below 40° C. Approximately 10 ml of the solution was then poured into 20 ml of water and heated to 100° C.; large quantities of gas were evolved. When gas evolution ceased, the remainder of the nitrating mixture was added in 10 ml portions with heating. When the last of the nitrating mixture had been added, the solution was cooled rapidly by placing the flask in an ice bath and by adding ice directly to the solution. The light brown precipitate was filtered and dried to afford 5.0 g (35%) of the title compound.