Diethyl (ethoxymethylene)malonate → HCID 178469654, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-iodo-4-(tetrahydro-2H-pyran-4-ylmethyl)aniline (1.0 g) and diethyl ethoxymethylenemalonate (0.70 mL) is heated to 130° C. for 1 h. The mixture is cooled to room temperature. Diphenyl ether (20 mL) is added and the reaction is heated to 250° C. for 1 h. The mixture is cooled and the resulting solid is collected and washed with hexanes. The crude product is chromatographed (Biotage flash 40M, eluant 2% MeOH/CH2Cl2) to yield 0.80 g (58%) of ethyl 4-hydroxy-8-iodo-6-(tetrahydro-2H-pyran-4-ylmethyl)-3-quinolinecarboxylate as a solid, m.p. 218-222° C. (dec).

Provenance & Evidence