Acetic Anhydride → Methyl 4-acetamidosalicylate

Participants

Reaction Steps

To a suspension of 4.17 g (0.025 mole) methyl 4-aminosalicylate (9) in 20 mL water, was added 3 mL (0.032 mole) acetic anhydride (Aldrich 11,004-3) while stirring. The mixture was heated at 80° for 30 minutes and cooled to room temperature. The precipitate was collected and added into 100 ml of 10% hydrochloric acid. This suspension was stirred at room temperature for 10 minutes, filtered and dried to give 4.3 g (82%) of a crude solid, which was recrystallized from H2O/CH3OH, yielding 3 g (70%) of 10 as white crystals, mp 153-154°. Infrared (IR) and NMR analysis gave the following results:

Provenance & Evidence