1,3-Dibromo-5,5-dimethylhydantoin → 6-Quinolinecarboxylic acid, 3-bromo-, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a mixture of quinoline-6-carboxylic acid methyl ester (0.50 g, 2.7 mmol) and tetrahydrofuran (10 mL) was added 1,3-dibromo-5,5-dimethyl hydantoin (0.76 g, 2.7 mmol) on an ice bath, and the solution was stirred at 50° C. for 4 hours. Water, an aqueous solution of saturated sodium bicarbonate and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was washed with brine, the solvent was then evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1), and the title compound (69 mg, 0.26 mmol, 10%) was obtained as a white solid.

Provenance & Evidence