Sulfuric Acid → 2-Hydroxy-6-methyl-5-nitropyridine

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To a suspension of 2-amino-5-nitro-6-methylpyridine (40.24 g, 260 mmol) was added concentrated sulfuric acid (48 mL). The homogeneous solution was cooled to 0° C., and sodium nitrate (26.97 g, 390 mmol) dissolved in 120 mL of water was added. The reaction mixture was warmed to room temperature over 4 hours, then cooled to 0° C. The resulting ivory precipitate was collected, washed with cold water, and dried at 40° C. in vacuo overnight to provide 39.05 g (97%) of the title compound. EA calculated for C6H6N2O3: C, 46.76; H, 3.92; N, 18.18. Found: C, 46.49; H, 3.94; N, 17.99.

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