Hydroxyamine hydrochloride → 6-Chloro-N-hydroxy-nicotinamidine

Participants

Reaction Steps

To a solution of sodium methoxide (15.6 g of 25-30% in methanol, 72 mmol) in methanol (70 mL) at 0° C. was added hydoxylamine hydrochloride (5.02 g, 72 mmol) and the mixture was then stirred at room temperature for 30 minutes. 5-cyano-2-chloropyridine (10 g, 72 mmol) was added and the reaction was heated to reflux for 3 hours. The reaction was cooled to room temperature, filtered to remove precipitated sodium chloride and the filtrate was evaporated to dryness. The residue was dissolved in ethanol in order to crystallise the product but this was unsuccessful, so the solvent was removed in vacuo to give the title compound as a white solid (12 g).

Provenance & Evidence