Trimethyl orthoformate → methyl 2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate

Participants

Reaction Steps

To a solution of 2-(hydrazinecarboxamido)isonicotinate (2.10 g, 10.0 mmol) in ethanol (140 mL) was added trimethyl orthoformate (2.43 g, 22.9 mmol) and p-toluenesulfonic acid monohydrate (0.70 g, 3.68 mmol) at ambient temperature. The reaction mixture was refluxed for 4 hours, cooled to ambient temperature and concentrated in vacuo to a minimum amount of volume. The solid was filtered, washed with cold methanol (20 mL) and dried in vacuo to give methyl 2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate as a colorless solid (1.68 g, 76%): MS (ES+) m/z 221.1 (M+1).

Provenance & Evidence