Phenyl 4-aminosalicylate → HCID 12083215, compound

Participants

Reaction Steps

This compound was prepared using the General Structural Outline for Synthesis of para-Aminosalicylic Acid Phenyl Ester Diacyl Derivatives. In a 50 mL pear shaped flask fitted for reflux were mixed para-aminosalicylic acid phenyl ester (1.45 g) and acetic anhydride (10 mL). Over 10 minutes, the mixture was brought to the boil, and refluxing was continued for 20 minutes. The mixture was allowed to cool to room temperature and stand for two hours, then poured out into a watchglass and allowed to dry. The resulting residue was ground with ether (10 mL) and the process repeated. The resulting white crystalline solid was the title compound (0.75 g, 38%), mp 142-143° C. (uncorr); IR v 3323, 1767, 1734, 1673, 1613, 1590, 1506, 1268, 1207, 1185, 1163, 1134, 1056, 1014, 1002, 944, 895, 862, 844, 748, 691 cm−1; NMR δ 10.5 (1H, br s), 8.2-7.1 (m, 8H), 2.2 (3H, s), 2.1 (3H, s).

Provenance & Evidence