Methyl iodide → Ethyl 7-bromo-1,4-dihydro-1-methyl-4-oxo-3-quinolinecarboxylate

Participants

Reaction Steps

A suspension of 4.04 g of ethyl 7-bromo-4-hydroxy-quinoline-3-carboxylate (J. Am. Chem. Soc. 71,3226, (1949)) and 4.71 g of potassium carbonate in 30 ml of dimethylformamide is treated with 9.68 g of methyl iodide at room temperature. The reaction mixture is heated to 90° and stirred at this temperature for 3 hrs. The reaction mixture is concentrated in a high vacuum. The residue is suspended in 50 ml of water, filtered off under suction and washed with 50 ml of water. Recrystallization of the crude product from ethanol/diethyl ether yields 3.67 g (86%) of ethyl 7-bromo-1-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate as a colourless solid. M.p. 189°-191°.

Provenance & Evidence