Hydroxyamine hydrochloride → 2-(4-Fluorophenyl)-1-pyridin-4-ylethanone oxime

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:23][OH:24]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:23][OH:24])=[CH:4][CH:3]=1

Participants

Procedure

21.5 g (0.1 mol) of 2-(4-fluorophenyl)-1-(4-pyridyl)-ethanone was suspended in 330 ml of 50% aqueous methanol. After addition of 36.1 g (0.44 mol) of sodium acetate and 22.0 g (0.32 mol) of hydroxylamine hydrochloride, the reaction mixture was refluxed for 1 h with stirring. On cooling in an ice bath, the title compound deposited as a beige-colored precipitate. The precipitate was filtered off, washed with dist. water and dried over P2O5 in vacuo. Yield: 14.3 g (62%).