Hydroxyamine hydrochloride → 5-Fluorosalicylaldoxime

Participants

Reaction Steps

A solution of sodium acetate trihydrate (1.94 g, 14.28 mmol) in H2O (8 mL) was added to a warm solution of 5-fluoro-2-hydroxy-benzaldehyde (1.0 g, 7.14 mmol) and NH2OH HCl (992 mg, 14.28 mmol) in 80% ethanol (30 mL). The reaction mixture was refluxed for 3 hr. Removal of ethanol, the mixture was cooled to rt, collected the precipitate and washed with water, dried to afford the title compound (920 mg, 83%). MS (DCI/NH3) m/z 217 (M+62)+. 1H NMR (500 MHz, DMSO-d6) δ ppm 6.89 (dd, J=9.15, 4.88 Hz, 1H) 7.07 (td, J=8.54, 3.05 Hz, 1H) 7.29 (dd, J=9.46, 3.05 Hz, 1H) 8.30 (s, 1H) 10.02 (brs, 1H) 11.46 (brs, 1H).

Provenance & Evidence