m-Chloroperbenzoic acid → Ethyl 2-chloroquinoline-6-carboxylate

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Reaction Steps

5.8 g (29 mmol) of ethyl quinoline-6-carboxylate was stirred in 80 ml of dichloromethane. 6.2 g of m-chloroperbenzoic acid was added to the obtained mixture under cooling with ice, and they were stirred at room temperature overnight. The mixture was washed with 10% aqueous sodium sulfite solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated. 70 ml of dichloromethane and 35 ml of phosphoryl chloride were added to the residue, and they were stirred at 50° C. overnight. The solvent was evaporated, and the residue was treated with dichloromethane as the extracting solvent by an ordinary method. After the purification by the silica gel chromatography (ethyl acetate/hexane), the title compound was obtained.

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