Hydroxyamine hydrochloride → 4-Chloro-nicotinonitrile

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%).

1. customThe solvent was evaporated
2. dissolutionthe residue was dissolved in chloroform (100 ml)
3. additionPhosphorus oxychloride (125 g) was added
4. temperaturethe mixture was heated under ref lux for 3 hrs
5. customThe solvent was evaporated
6. additionthe residue was added to water (200 ml), which
7. extractionThe mixture was extracted with ethyl acetate (200 ml×2)
8. dry with materialthe organic layer was dried (MgSO4)
9. customThe solvent was evaporated under reduced pressure

ORD record

ord-60cae545593e472089f70c00f23e4af0

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067537B2