Potassium Iodide → HCID 117776656, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-oxo-8-chloro-1,4-dihydroquinoline-3-carboxylate (1.0 g), potassium iodide (0.66 g) and sodium carbonate (1.1 g) in DMF (20 mL) was added 1-(chloromethyl)-4-methoxybenzene (0.7 mL), and the mixture was stirred at 70° C. overnight. The reaction mixture was diluted with water and ethyl acetate, and the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was solidified with a diisopropyl ether-ethyl acetate mixed solution. The obtained solid was dissolved in ethanol-THF (1:1, 12 mL), 1 N aqueous sodium hydroxide solution (6 mL) was added, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was diluted with water, neutralized with 1 N hydrochloric acid (10 mL), and the precipitate was collected by filtration, washed with water, and dried to give the title compound (0.52 g).

Provenance & Evidence