Nitric Acid → 2-Bromo-3-methoxy-6-nitropyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-3-methoxypyridine (7.0 g, 37 mmol) in H2SO4 (70 mL) was added fuming HNO3 (2.4 ml, 37 mmol) dropwise at 0° C. under N2 atmosphere. The mixture was stirred at 60° C. for 2 hours. After cooling to room temperature, the mixture was quenched with water (100 mL). The insoluble solid was collected by filtration and washed with water (100 mL). The solid was dissolved in ethyl acetate (100 mL) and basified to pH to 8 with saturated aqueous NaHCO3. The aqueous layer was extracted with ethyl acetate (150×3 mL). The combined organics layers were washed with brine, dried over anhydrous Na2SO4, evaporated in vacuo and purified by chromatography on silica gel (10% ethyl acetate in petroleum ether) to give 2-bromo-3-methoxy-6-nitropyridine (5.0 g, 55%). 1H-NMR (300 MHz, CDCl3) δ 8.27 (d, J=8.7, 1H), 7.32 (d, J=8.7, 1H), 4.06 (s, 3H).

Provenance & Evidence