Aluminum(III) Chloride → HCID 178479873, compound

Participants

Reaction Conditions

Reaction Steps

(Method K) (Demethylation) The appropriate 6-methoxyquinoacridine was suspended in benzene and anhydrous aluminium chloride added (3 eq). The mixture was heated to 80° C., giving a red oily suspension and bright green haze on the solvent, until complete reaction was seen by tlc (0.2 mL sample, 0.5 mL methanol quench, 0.2 mL sat. aq. NaHCO3 neutralisation, neat EtOAC eluent) then allowed to cool to room temperature. Methanol was added slowly with ice cooling of the suspension and the stirring continued until all red oil was gone. The solvent was evaporated under reduced pressure, and the residue treated with sat. aq. sodium hydrogen carbonate. The organics were separated form the crude filtrate by soxhlet extraction with ethyl acetate. Filtration of the precipitate on cooling gave the desired compound.

Provenance & Evidence