Aniline → Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

31.7 g (147 mmol) of 2-Ethoxymethylene-malonic acid diethyl ester and 13.7 g (147 mmol) of aniline were stirred neat at 110° C. for 1 h, then 300 mL of diphenyl ether was added and the temperature of the oil bath was raised to 260° C. for 2 h. The solution was then cooled down to rt, diluted with 600 mL of hexanes and filtered. The solids were washed with 200 mL of hexanes and dried to yield 23.7 g of the product as a light brown powder. LC-MSD, m/z for C12H11NO3 [M+H]+=218.2, HPLC retention time: 2.5 min.

Provenance & Evidence