Benzonitrile, 4-bromo- → 4-Bromo-N'-hydroxybenzene-1-carboximidamide

Temperature

90 °C

To a solution of 4-bromobenzonitrile (5.0 g, 27.5 mmol) in ethanol (42 ml) at room temperature, hydroxylamine hydrochloride (1.91 g, 27.5 mmol) and DIPEA (4.8 ml, 27.5 mmol) were added. The reaction mixture was stirred at 90° C. for 5 hours. After cooled to room temperature, the resulting mixture was concentrated to yield a colorless viscous liquid. The liquid was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate, filtered and then concentrated to give a crude compound, which was washed with n-hexane to yield product 15 as a white solid (5.0 g).

1. temperatureAfter cooled to room temperature
2. concentrationthe resulting mixture was concentrated
3. customto yield a colorless viscous liquid
4. extractionThe liquid was extracted with ethyl acetate
5. dry with materialthe organic layer was dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a crude compound, which
9. washwas washed with n-hexane

ORD record

ord-3a6f27639a944d6f898938c65c4a7fb1

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415482B2