N,N-Dimethylaniline → HCID 15458589, compound

Participants

Reaction Steps

To a suspension of 2,3-dimethyl-4-hydroxy-8-methoxyquinoline (3.0 g) in phosphoryl chloride was dropwise added N,N-dimethylaniline (3.58 g) under ice-cooling, and the mixture was stirred for 15 minutes at the same temperature, for 30 minutes at ambient temperature and then for 1 hour at 70° C. The solvent was removed, and saturated sodium bicarbonate solution and 10% solution of methanol in dichloromethan were added to the residue. The organic layer was dried over magnesium sulfate and concentrated. The residue wa purified by flash chromatography (Ethyl acetatein-hexane=1:2 v/v) to give 4-chloro-2,3-dimethyl-8-methoxyquinoline (3.02 g).

Provenance & Evidence