HCID 15571672, compound → 3-Methoxyacridine

Participants

Reaction Steps

A solution of 93.34 g of 3-methoxy-9-chloroacridine (0.38 mol) in 2 L of 5 N HCl was stirred at reflux for 40 h. The reaction mixture was cooled to room temperature and the precipitate was collected by suction filtration, washed with 1 L of water, and dried. The solid was stirred in 1 L of methanol and the insoluble precipitate was collected by filtration to afford 15.3 g of the desired 3-methoxy-acridine. The filtrate was concentrated in vacuo and chromatographed on silica gel in 20% methanol in CH2Cl2 to afford a dark brown solid. The solid was triturated in 200 mL of methanol and the insoluble precipitate was collected by filtration to afford a second crop of product. The filtrate was concentrated to a thick solution, and a third crop of product was collected by filtration. The second and third crop of product were combined to give 2.6 g of 3-methoxyacridone, for a combined total of 17.9 g (21%).

Provenance & Evidence