Dimethylamine → 3-(2-Oxo-1,2-dihydropyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylaldehyde (cis and trans mixture) (1.15 g) and 1-carbamoylmethylpyridinium chloride (0.80 g), 50% aqueous dimethylamine (0.44 g) and methanol (10 ml) was refluxed for 3 hours. The reaction mixture was evaporated in vacuo and the residue was heated for 10 minutes at 200° C. The resulting mixture was chromatographed on silica gel (80 g) with a mixture of chloroform and methanol (100:1). The fractions containing ton silica gel (80 g) with a mixture of chloroform and methanol (100:1). The fractions containing the object compound were combined and evaporated in vacuo and recrystallized from ethanol to give 3-(2-oxo-1,2-dihydropyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.33 g).

Provenance & Evidence