3-Hydroxy-6-methyl-2-nitropyridine

1121-78-4

15128-90-2

General procedure for the synthesis of 3-hydroxy-6-methyl-2-nitropyridine from 3-hydroxy-6-methylpyridine: 3-hydroxy-6-methylpyridine (23.6 g, 216 mmol) was dissolved in concentrated sulfuric acid (50 mL) and cooled to 0 °C. Fuming nitric acid (50 mL) was added slowly over a period of 1 hour. The reaction mixture was stirred at room temperature for 1 hour and then poured into ice (400 g) and the precipitate was collected by filtration. The resulting solid was dissolved in ethyl acetate and the organic layer was washed with brine (100 mL). The organic phase was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give 12.1 g of the title compound (36.3% yield). The melting point of the product was 102-105 °C. 1H NMR (DMSO-d6, 300 MHz) δ: 2.44 (s, 3H), 7.52 (d, J = 8.5 Hz, 1H), 7.58 (d, J = 8.5 Hz, 1H). Mass spectrum (ESI-Q1MS) m/e 153 (M-H)+. Elemental analysis calculated values (C6H6N3O3): C, 46.76; H, 3.92; N, 18.18. Measured values: C, 46.65; H, 3.98; N, 18.10.