3-Fluorobenzonitrile → HCID 178513300, compound

Temperature

70 °C

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).

1. temperatureThe reaction mixture was cooled to room temperature
2. concentrationconcentrated to half the original volume
3. additionThe residue was added to a mixture of dichloromethane (200 mL) and water (60 mL)
4. customthe organic phase was separated
5. extractionThe aqueous phase was extracted further with dichloromethane (2×50 mL)
6. washthe combined organic phase was washed with water (75 mL)
7. washwashed with brine (75 mL)
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated

ORD record

ord-93cbb9c078cb45fb88088b7856ae79a1

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07485722B2