Hydrochloric Acid → HCID 178426865, compound

Participants

Reaction Steps

To a mixture of 5-dimethoxymetyl-3,6-dimethyl-2-pyridinecarboxaldehyde (53 mg, 0.25 mmol) and 2,4-thiazolidindione (44 mg, 0.38 mmol) in ethanol (5 mL) was added piperidine (0.038 mL, 0.38 mmol), and the mixture was heated to reflux for 16 h. Hydrochloric acid (1 mol/L; 0.4 mL) and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried on anhydrous sodium sulfate, and concentrated under reduced pressure. To the residue were added tetrahydrofuran (4 mL) and hydrochloric acid (1 mol/L; 0.5 mL), and the mixture was stirred at room temperature for 7 h. Water was added, and the precipitated products were collected by filtration to afford 5-formyl-3,6-dimethylpyridin-2-ylidene-2,4-thiazolidinedione (43 mg, 66%).

Provenance & Evidence