Hydrochloric Acid → 2-Amino-1-(4-chlorophenyl)ethan-1-one hydrochloride

To a stirred solution of 2-bromo-4'-chloroacetophenone (10.34 g, 43.40 mmol) and 18-crown-6 (1.16 g, 4.34 mmol) in acetonitrile (150 mL) at room temperature (RT) is added sodium diformylamide (12.51 g, 131.6 mmol). After 3 h at RT and 2 h at 40° C., the suspension is diluted with water (100 mL) and extracted with ethyl acetate (4×150 mL). The combined organics are washed with brine, dried (magnesium sulfate), and concentrated to afford waxy yellow solids. These are taken up in absolute ethanol (150 mL), the stirred solution is treated with concentrated hydrochloric acid (15.00 mL, 174 mmol), and the mixture is heated to reflux for 1.5 h. The suspension is cooled to RT, filtered, and the solids are washed with ethyl acetate. Drying in vacuo at RT afforded the title compound as white solids.

1. extractionextracted with ethyl acetate (4×150 mL)
2. washThe combined organics are washed with brine
3. dry with materialdried (magnesium sulfate)
4. concentrationconcentrated
5. customto afford waxy yellow solids
6. temperaturethe mixture is heated
7. temperatureto reflux for 1.5 h
8. filtrationfiltered
9. washthe solids are washed with ethyl acetate
10. customDrying in vacuo at RT

ORD record

ord-eade185c108d439ab3588fd6a27b5891

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06090825