Pyridine → 6-Oxo-1,6-dihydropyridazine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

6-Oxo-1,6-dihydropyridazine-3-carboxamide (J. Chem. Soc. 1948, 2195) (1.1 g, 8.0 mmol) was suspended in dichloromethane (20 mL), cooled to 0° C. then pyridine (1.3 mL, 16 mmol) and trifluoroacetic anhydride (1.2 mL, 8.4 mmol) were added and the reaction was stirred at room temperature for 1 hour. A further 5 mL of pyridine was added to aid solubility and then the reaction was warmed to room temperature and stirred overnight. The mixture was diluted with water (100 mL) and then extracted with dichloromethane (3×100 mL). The combined organic extracts were dried (Na2SO4), the solvent was removed in vacuo, with residual pyridine removed by azeotroping with toluene. The residue was purified by flash chromatography on silica gel (dichloromethane/methanol 95:5 as eluant) to give the title compound as an off-white solid (0.8 g).

Provenance & Evidence