Hydrochloric Acid → Phenyl acridine-9-carboxylate

Participants

Reaction Steps

Acridine-9-carboxylic acid (5 g) is suspended in thionyl chloride (75 ml). The mixture is stirred under reflux for four hours. The excess of thionyl chloride is removed by distillation. The residue is suspended in pyridine (75 ml) and the mixture stirred at room temperature for ten minutes. Phenol (4.5 g) is added to the suspension. The resulting reaction mixture is stirred at room temperature for sixteen hours. The resulting solution is poured into one normal hydrochloric acid (200 ml). The precipitate that forms (6.5 g) is isolated by filtration, and recrystallized from benzene/cyclohexane. m.p. 192° C.; IR (KBr): 1750, 1177 cm-1. MS: 299, 206, 178, 152, 151. 1H-NMR: δ7.5-8.5.

Provenance & Evidence