Aluminum(III) Chloride → 6-Fluoroisoquinoline

Participants

Reaction Steps

41.6 g of AlCl3 were suspended in 400 mL of dichloromethane. At room temperature, a solution of 22.95 g N-(2,2-dimethoxy-ethyl)-N-(4-fluoro-benzyl)-4-methyl-benzenesulfonamide (2) in 150 ml of dichloromethane was added. Stirring was continued at room temperature overnight, the solution was poured on ice, the layers were separated, the aqueous phase was extracted twice with dichloromethane and the combined organic layers were then washed twice with sodium bicarbonate solution. The organic layer was dried over magnesium sulfate, evaporated to dryness and the obtained crude product (8.75 g) was purified by silica gel chromatography to yield 2.74 g of compound 3. Rt=0.30 min (Method C). Detected mass: 148.1 (M+H+).

Provenance & Evidence