3-Fluorobenzonitrile → HCID 178513300, compound

Participants

Reaction Conditions

Reaction Steps

3-Fluorobenzonitrile (2.5 g, 0.021 mol), diisopropylethyl amine (10.8 mL, 0.062 mol) and hydroxylamine hydrochloride (4.3 g, 0.062 mol) were mixed in ethanol (30 mL). The reaction mixture was stirred at 70° C. overnight. The reaction mixture was cooled to room temperature and concentrated to half the original volume. The residue was added to a mixture of dichloromethane (200 mL) and water (60 mL). The mixture was basified to pH 9 using 2N NaOH and the organic phase was separated. The aqueous phase was extracted further with dichloromethane (2×50 mL) and the combined organic phase was washed with water (75 mL), washed with brine (75 mL), dried over sodium sulfate and concentrated to give the product as a yellow solid (2.8 g, 89%). 1H NMR (300 MHz, CDCl3): δ 8.05 (bs, 1H), 7.39 (m, 3H), 7.16 (m, 1H), 4.88 (bs, 2H).

Provenance & Evidence