Sodium Thiosulfate → Ethyl 6-bromomethyl-3-methylquinoline-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3,6-dimethylquinoline-2-carboxylate (1.0 g) in tetrachloromethane (10 ml) were added N-bromosuccimide (815 mg) and 2,2'-azobis (2,4-dimethyl-4-methoxyvaleronitrile) at ambient temperature under nitrogen atmosphere, and the mixture was heated at 90° C. for 1 hour. The reaction mixture was poured into 5% sodium thiosulfate solution and extracted with dichloromethane. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography (n-hexane--ethyl acetate) to give ethyl 6-bromomethyl-3-methylquinoline-2-carboxylate (802 mg) as a solid.

Provenance & Evidence