Pyridine → HCID 22933738, compound

Participants

Reaction Conditions

Reaction Steps

A 20%-aqueous sulfuric acid solution (4 ml) was added dropwise to a solution of 4-[(2,2-dimethylpropanoyl)amino]-2-methoxy-3-methylphenyl methanesulfonate (223 mg, 0.707 mmol) in n-butanol (2 ml) at room temperature, and the resulting mixture was heated to 100° C. After 14 hours, the reaction solution was poured onto ice (50 ml) and adjusted to pH 11 with an aqueous sodium hydroxide solution. The resulting mixture was extracted with ethyl acetate (50 ml×3) and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure, and to a solution of the resulting residue in ethyl acetate (5 ml) were added pyridine (0.069 ml, 0.848 mmol) and acetic anhydride (0.073 ml, 0.778 mmol) at room temperature. The resulting mixture was heated to 60° C. After 2 hours, the reaction solution was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate→chloroform/ethyl acetate) to obtain 4-(acetylamino)-2-methoxy-3-methylphenyl methanesulfonate (154 mg, 79%).

Provenance & Evidence