Potassium Carbonate → 2-Methoxy-3,6-dimethyl-5-nitropyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 2-(6-methoxy-5-methyl-3-nitropyridin-2-yl)acetate (62.5 g, 276 mmol), K2CO3 (20.0 g, 145 mmol), and DMF (100 mL) was heated with stirring in a hot water bath to 90° C. for 1 h. Gas evolution was noted during the heating period and had ceased after 1 hour. The mixture was poured into stirred ice water (600 mL), with washing of the reaction flask with a small volume of acetone. The resulting precipitate was collected by filtration and air dried to give 2-methoxy-3,6-dimethyl-5-nitropyridine (48.5 g, 96% yield) as a tan solid: 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 4.02 (s, 3H), 2.76 (d, 3H), 2.19 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 163.37, 151.63, 139.44, 135.02, 119.39, 54.45, 24.18, 15.16. An analytical sample was recrystallized from hexanes to give tan needles: mp 85.9-90.5° C. Anal. calcd. for C8H10N2O3: C, 52.74; H, 5.53; N, 15.37. Found: C, 52.82; Fr, 5.28; N, 15.45.

Provenance & Evidence