Pyridine-2-carbonitrile → HCID 54759228, compound

Participants

Reaction Conditions

Reaction Steps

A dry round-bottom flask was charged with 2-cyanopyridine (0.500 g, 4.8 mmol), 5-amino-2-cyanopyridine (0.572 g, 4.8 mmol), and 64% aqueous hydrazine hydrate (0.932 mL, 19.2 mmol). The flask was fitted with a reflux condenser, and the mixture was heated to 90° C. for 12 hr. The reaction mixture was cooled to room temperature. The resulting orange precipitate was isolated by filtration, washed with cold H2O, and dried under vacuum. The crude orange solid was concentrated in vacuo onto deactivated silica gel and chromatographed using a gradient (0-60%) of acetone in hexanes to give 377 mg (1.5 mmol, 31%) of 6-(6-pyridin-2-yl-1,4-dihydro-[1,2,4,5]tetrazin-3-yl)-pyridin-3-ylamine as an orange solid, mp 158-160° C.

Provenance & Evidence