Toluene → HCID 86590247, compound

Participants

Reaction Steps

A mixture of toluene (80 mL), piperidine (380 μL), acetic acid (380 μL), 3-(1,4,4,6-Tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-trifluoromethoxy-benzaldehyde (7.5 g, 19.16 mmol) and 2,4-thiazolidinedione (2.25 g, 19.16 mmol) was heated at reflux overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with water and brine, dried over MgSO4. The residue was recrystallized successively from ethanol, dichloromethane/hexane and ethanol to afford 4.3 g (46%) of 5-[3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-trifluoromethoxy-benzylidene]-thiazolidine-2,4 dione. mp 182–184° C.

Provenance & Evidence