Sodium Bicarbonate → 5-Hydroxy-2-(trifluoromethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

3-Amino-6-trifluoromethylpyridine (9.86 g, 61 mmol) was dissolved in concentrated sulphuric acid (70 ml) and diluted with water (70 ml), then cooled to −8° C. A solution of sodium nitrite (5.18 g, 75 mmol) in water (50 ml) was slowly added, and the mixture warmed to 0° C. for 15 minutes. The solution was then poured into sulphuric acid (10 M, 250 ml) and heated to 110° C. for 1 h. After cooling, the pH was adjusted to 6 with saturated sodium bicarbonate solution, and the solution extracted with ethyl acetate (2×300 ml). The extracts were dried (MgSO4) and concentrated to give the product as a yellow solid (7.15 g, 44 mmol, 72% yield).

Provenance & Evidence