Indomethacin → Acemetacin

Participants

Reaction Conditions

Reaction Steps

One hundred grams of indomethacin, 91.25 g of potassium fluoride and 13.5 g of sodium propionate were suspended in 500 ml of dimethylformamide, followed by an addition of 64.31 g of t-butyl chloroacetate. The resultant mixture was stirred and then stirred for 1 hour in a water bath of 90° C. After cooling, the mixture was poured into 5 liters of a 10% solution of sodium carbonate in water, followed by an addition of water to make the total volume be 20 liters. The resulting yellowish solid deposit was separated and then taken up in 1.65 liters of benzene. The thus-prepared solution was washed with water and, after drying, the solvent was driven off. The residue was recrystallized from n-hexane, thereby obtaining 126.1 g of the t-butyl ester of acemetacin as pale yellowish crystals (yield: 95.6%)

Provenance & Evidence