Acetone → HCID 10492615, compound

Participants

Reaction Conditions

Reaction Steps

A 3-liter, three-neck round-bottom flask was charged with 76.5 g (0.5 mole) of 4-aminosalicylic acid in 400 ml of reagent acetone. The flask was flushed with nitrogen and sealed under a nitrogen balloon as stirring was started. A solution of 50 g (0.51) of maleic anhydride dissolved in 400 ml of reagent acetone was added to maintain the temperature at reflux (about 57° C.) with added heat for 1 hour, which gave a very thick pale green precipitate. The flask was then charged with 153 g of acetic anhydride and 9 g of sodium acetate and reflux was continued for an additional 11/2 to 2 hours. The acetone was stripped from the reaction mixture and 1-liter of distilled water added to wash the solid. The solid was suction-filtered and dried at 100° C. under 29 inches of Hg vacuum. The yield of brown solid was near quantitative and melted at 110-119° C. The 400 MHz proton NMR analysis showed maleimide and O-acetyl formation.

Provenance & Evidence