4-Aminosalicylic Acid → 4-Acetamidosalicylic acid

Participants

Reaction Steps

To a stirred, refluxing suspension of 4-aminosalicylic acid (76.57 g, 0.5 mmol) in 250 mL absolute ethanol was added dropwise, over a 30 minute period, acetic anhydride (83.2 g, 0.815 mmol). After the addition was complete, the mixture was refluxed for another 15 minutes and then cooled. The product collected by filtration, washed with small amount of ethanol and dried on air to give 72.3 g (74.15%) of the title compound as a grey solid mp 242°14 4° C. Previously reported mp: 234°-5° C. (P. Barraclough et al. Eur. J. Chem. 25, p 467, 1990).

Provenance & Evidence