Sulfuric Acid → 5-Hydroxypyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Concentrated sulfuric acid (21.0 mL) was added to a suspension of 3-amino-6-cyanopyridine (5.00 g, 42.0 mmol) in water (75.0 mL), and then a 1.6 M aqueous solution of sodium nitrite (29.0 mL, 46.4 mmol) was slowly added dropwise thereto under ice water cooling. This suspension was stirred for 6 hours at 100° C. The reaction mixture was cooled to room temperature, and then was diluted with ethyl acetate (100 mL). The organic layer was washed sequentially with water and saturated brine, and was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1, v/v). Thus, the title compound was obtained.

Provenance & Evidence