Diethyl (ethoxymethylene)malonate → HCID 178469641, compound

Participants

Reaction Conditions

Reaction Steps

A neat mixture of 2.8 g of compound of 3-methylthioaniline and 4.0 g of diethyl ethoxymethylenemalonate is heated at 135° C. under a slow argon sweep for 1 h, then diluted with 25 mL of diphenyl ether and heated to 260° C., with maintenance of the argon sweep, and kept at that temperature for 90 min. The mixture is then cooled to ca 100° C. and added to 300 mL of stirred 1:1 ether-hexane. The precipitate is filtered, washed with hexane, and dried in vacuo to provide 1.35 g of crude material as a tan solid, which is recrystallized from acetic acid-water to afford 1.06 g of ethyl 4-hydroxy-7-(methylsulfanyl)-3-quinolinecarboxylate.

Provenance & Evidence