Trifluoroacetic acid → Ethyl 3-amino-4-cyanopyridine-2-carboxylate

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A stirred solution of ethyl 2-cyano-2-(formylamino)acetate J. Org. Chem., 1979, 44, 3835; 0.47 g, 0.003 mol), acrylonitrile (1.2 ml, 0.018 mol) and trifluoroacetic acid (0.02 ml, 0.0003 mol) in 1,2-dichloroethane (4 ml) was heated under reflux for 3 days. The solvent was removed by evaporation under vacuum, the residue dissolved in dichloromethane (30 ml) and the resulting solution washed with saturated aqueous sodium bicarbonate solution (30 ml). The aqueous phase was washed with dichloromethane (30 ml) and the organic solutions then combined, dried (MgSO4) and evaporated under vacuum. Chromatography of the residue on silica gel (12 g), eluting with dichloromethane:methanol (100:1), followed by crystallisation from acetone: hexane, gave the title compound as a colourless solid (0.12 g, 21%), m.p. 114°-116° C. Found: C,56.89; H,4.75; N,22.08. C9H9N3O2 requires C,56.54; H,4.75; N,21.98%.

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