Hydrochloric Acid → Rosiglitazone hydrochloride

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (6.0 g) and propan-2-ol (120 ml) was stirred and heated to 50° C. under a nitrogen atmosphere. A solution of hydrogen chloride in propan-2-ol (5-6 N, 5.0 ml) was added and the stirred mixture warmed to 70° C., at which point a clear solution was observed. After cooling to 45° C. over a period of one hour the resulting cloudy solution was warmed to 60° C. and maintained at this temperature for a period of 1 hour. The resulting thick white suspension was cooled to 30° C. and the solid product collected by filtration, washed with propan-2-ol (25 ml) and dried under vacuum, over phosphorus pentoxide for 16 hours to give the title compound as a white crystalline solid (5.7 g).

Provenance & Evidence