Hydrochloric Acid → HCID 66746690, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-fluoro-6-methoxy-quinolin-3-ylamine (prepared according to procedures described in FR2862301, 830 mg, 4.3 mmol, 1.0 eq) and concentrated hydrochloric acid (12N, 3.0 g, 30.2 mmol, 7.0 eq) is stirred at 4° C. before the addition of sodium nitrite (313 mg, 4.7 mmol, 1.1 eq) in water (24 mL). After 2 hours stirring at 4° C., the resulting mixture is added dropwise to a stirred solution of concentrated sulfuric acid (8.2 mL) and water (24 mL) at 90° C. within 10 minutes. After 1 hour stirring at 90° C. the reaction mixture is cooled down to room temperature, neutralized with sodium hydrogen carbonate and extracted with ethyl acetate (3×80 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is recrystallized in methanol to afford 7-fluoro-6-methoxy-quinolin-3-ol as an off-white solid (0.60 g, 72% yield).

Provenance & Evidence