Acetaminophen → 3-Pyridinecarboxylic acid, 4-(acetylamino)phenyl ester

Participants

Reaction Steps

TEA (1.2 ml, 8.6 mmol, 5.0 eq) was added to a solution of paracetamol [4147] (0.26 g, 1.7 mmol, 1.0 eq) in dry THF under argon atmosphere. At 0° C., nicotinoyl chloride hydrochloride [296] (1.53 gm, 8.6 mmol, 5.0 eq) was added to the above reaction mixture. The reaction mixture was stirred at room temperature for 24 h. After 24 h, organic solvent was evaporated under vacuum and residue was dissolved in dichloromethane (50 ml) and washed with a 10% solution of NaHCO3 (15 ml) and then with brine (10 ml) followed by drying of organic layer over anhydrous sodium sulfate. Evaporation of the solvents provided white solid which was purified by silica gel column chromatography (4% MeOH: DCM, 100-200 mesh silica) to give the product 4-acetamidophenyl nicotinate [297] (0.34 g, 78%).

Provenance & Evidence