3-Pyridinecarboxamide,2-amino-(9CI)

5345-47-1

13438-65-8

The general procedure for the synthesis of 2-aminopyridine-3-carboxamide from 2-aminonicotinic acid was as follows: 2-aminonicotinic acid (1.38 g, 10.0 mmol) was suspended in DMF (50 mL) and HOBt (1.35 g, 10.0 mmol), NH4Cl (1.07 g, 20.0 mmol), EDC-HCl (2.88 g, 15.0 mmol) and triethylamine (2.78 mL, 20.0 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was removed by distillation under reduced pressure and CH2Cl2 (150 mL) and saturated aqueous NaHCO3 solution (150 mL) were added to the residue. The organic phase was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by rapid chromatography on silica gel (3→5% MeOH-CH2Cl2) to afford 2-aminopyridine-3-carboxamide (1.21 g, 8.85 mmol, 89% yield) in white powder form. The product was characterized by 1H NMR (DMSO-d6) and ESI-MS: 1H NMR (DMSO-d6) δ: 6.55 (1H, dd, J = 7.7,4.8 Hz), 7.17 (2H, s), 7.30 (1H, s), 7.92 (2H, dd, J = 7.7,1.8 Hz), 8.06 (1H, dd, J = 4.8, 1.8 Hz); ESI-MS. 1.8 Hz); ESI-MS m/z: 138 (M + H)+.