Hydroxyamine hydrochloride → 4-Chloro-nicotinonitrile

Participants

Reaction Steps

The compound (19) (27.0 g, 0.19 mol), hydroxylamine hydrochloride (13.01 g, 0.19 mol) and sodium acetate (15.6 g, 0.19 mol) were suspended in methanol (100 ml) and the mixture was stirred at room temperature for 2 hrs. The solvent was evaporated and the residue was dissolved in chloroform (100 ml). Phosphorus oxychloride (125 g) was added and the mixture was heated under ref lux for 3 hrs. The solvent was evaporated and the residue was added to water (200 ml), which was adjusted to pH=7 with sodium carbonate. The mixture was extracted with ethyl acetate (200 ml×2) and the organic layer was dried (MgSO4). The solvent was evaporated under reduced pressure to give the title compound (18 g, 68%).

Provenance & Evidence