2-Cyano-6-methoxy benzothiazole → 2-Cyano-6-hydroxybenzothiazole

Participants

Reaction Conditions

Reaction Steps

Pyridine hydrochloride (2.32 g) was added to 2-cyano-6-methoxybenzothiazole 31 (51.4 mg, 0.271 mmol) and heated to 200° C. in an argon atmosphere to dissolve the pyridine hydrochloride, and the reaction mixture was stirred for 30 minutes. The reaction mixture was allowed to cool, and then 1 M hydrochloric acid (50 ml) was added. After extraction with ethyl acetate (3×50 ml) and drying of the organic layer with anhydrous sodium sulfate, the result was concentrated in vacuo. The resulting residue was purified by preparative thin-layer silica gel chromatography {one 20 cm×20 cm×1.75 mm plate; hexane-ethyl acetate (1:1)}, yielding 2-cyano-6-hydroxybenzothiazole 32 (47.2 mg, 99%) as a pale yellow solid.

Provenance & Evidence