Pyridine → 3-Bromoquinoline-6-carboxylic acid

Participants

Reaction Steps

To a suspension of quinoline-6-carboxylic acid (2.77 g, 16.0 mmol) in CCl4 (20 ml) in a flask wrapped with Al foil was added bromine (987 uL, 19.2 mmol) dropwise. The resulting mixture was stirred at rt for 30 min, then heated under reflux for 30 min. A solution of pyridine (1.55 mL, 19.2 mmol) in CCl4 (4 mL) was added dropwise at refluxing temperature. Then the reaction mixture was heated under reflux for 4 h. The reaction mixture was treated with 3 N NaOH until all the precipitates were dissolved. The aqueous layer was separated and washed with DCM once more, then acidified with 3 N HCl. The resulting orange precipitates were filtered, and washed with H2O, and a small amount of MeOH to afford the titled compound as an off-white solid (3.36 g).

Provenance & Evidence