Acetic Anhydride → HCID 18447366, compound

Participants

Reaction Steps

Acetic anhydride (0.04 ml) was added to a solution of the 2-(1H-indazol-5-yloxy)aniline (34 mg, 0.151 mmol) obtained in Example 476 in pyridine (1 ml) at room temperature, and the resulting mixture was stirred at room temperature for 2 hours. The reaction solution was cooled to 0° C. and a saturated aqueous sodium hydrogencarbonate solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was dissolved in a mixed solution of tetrahydrofuran (1 ml) and methanol (1 ml), followed by adding thereto 1N aqueous sodium hydroxide solution (1 ml). The resulting mixture was stirred at room temperature for 1 hour. The reaction solution was added to a saturated aqueous sodium chloride solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (chloroform/methanol) to obtain N-[2-(1H-indazol-5-yloxy)phenyl]acetamide (32 mg, 79%).

Provenance & Evidence