Bicarbonate Ion → HCID 21192606, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing diethyl 2-{[4-(4-morpholinylmethyl)(tetrahydro-2H-pyran-4-yl)anilino]methylene}malonate (0.41 g) is treated with polyphosphoric acid (1.5 g). The reaction mixture is heated to 100° C. under a flow of nitrogen gas. After 1 hour the reaction is cooled to room temperature. The reaction mixture is carefully added to a vigorously stirred mixture of dichloromethane and saturated aqueous bicarbonate. The layers are separated and the basic aqueous layer is extracted with three additional portions of dichloromethane. The combined organic layers are washed with water, brine, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica eluting with 2% to 6% methanol in dichloromethane to afford 0.24 g of ethyl 6-(4-morpholinylmethyl)-4-oxo-1-tetrahydro-2H-pyran4-yl-1,4-dihydro-3-quinolinecarboxylate as a tan solid.

Provenance & Evidence