Nitric Acid → 3-Methoxy-5-nitropyridin-2-ol

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (8.6 g, 0.215 mole) and 2,3-dihydroxypyridine (22.0 g, 0.20 mole) were added to distilled water (75 ml). After cooling to 5° C., dimethylsulfate (25.0 g, 0.21 mole) was added dropwise; the reaction mixture was stirred for 20 hours while slowly warming to room temperature. The water was removed in vacuo (approximately 65° C.) to obtain a syrup which was dissolved in concentrated sulfuric acid (50 to 60 ml) at 5° C. A cold mixture of concentrated nitric acid (20 ml) in concentrated sulfuric acid (20 ml) was added at a rate to maintain the reaction mixture between 10° to 15° C. After the addition was complete, the mixture was stirred for 30 minutes at 5° C. and then poured onto ice (approximately 400 ml). The resulting red precipitate was collected by filtration and recrystallized from water; yield, 5.8 g (17 percent).

Provenance & Evidence