Nitric Acid → 6-Methyl-2-nitropyridin-3-ol

Participants

Reaction Conditions

Reaction Steps

5-Hydroxy-2-methylpyridine (23.6 g, 216 mmole)was dissolved in conc. H2SO4 (50 mL) and cooled to 0° C. Fuming HNO3 (50 mL) was added over one hour. The solution was stirred at room temperature for one hour, poured onto ice (400 g), and filtered. The solids were dissolved in EtOAc washed with brine (100 mL). The organic extracts were dried (MgSO4), and the solvent was evaporated to yield 12.1 g (36.3%) of the title compound. mp 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). MS (ESI -Q1MS) m/e 153(M-H)+. Anal. calcd. for C6H6N2O3C, 46.76 H, 3.92; N, 18.18 Found: C, 46.65 H, 3.98; N, 18.10.

Provenance & Evidence