Hydroxyamine hydrochloride → HCID 58986275, compound

Hydroxylamine hydrochloride (2.1 g, 0.03 mol) was added to a solution of 3-phenyl-1-[4-(trifluoromethyl)phenyl]propan-1-one (Journal of the American Chemical Society 1994, 116(6), 2312-17, 2.8 g, 0.01 mol) in EtOH (30 ml). The solution was heated to reflux temperature for 18 hours. After cooling to RT, the solvent was evaporated under reduced pressure and the residue diluted with EtOAc (30 ml). The organic phase washed with water (3×20 ml), dried over Na2SO4 and concentrated. The crude reaction was then dissolved in EtOH (20 ml) and Raney Nickel (5 spoons) added. The reaction mixture was stirred for 2 days under a balloon of nitrogen and then filtered through a pad of celite. The filtrate was concentrated and purified by chromatography on silica gel eluting with 50% AcOEt/Hexane to afford the title compound (0.8 g, 28%); 1H NMR δ (ppm)(CDCl3, 360 MHz): 7.64 (2 H, d, J=7.7 Hz), 7.47 (2 H, d, J=7.7 Hz), 7.32 (2 H, m), 7.22-7.19 (3 H, m), 4.00 (1 H, t, J=6.7 Hz), 2.73-2.57 (2 H, m), 2.07-2.00 (2 H, m).

1. temperatureThe solution was heated
2. temperatureto reflux temperature for 18 hours
3. customthe solvent was evaporated under reduced pressure
4. additionthe residue diluted with EtOAc (30 ml)
5. washThe organic phase washed with water (3×20 ml)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe crude reaction
9. filtrationfiltered through a pad of celite
10. concentrationThe filtrate was concentrated
11. custompurified by chromatography on silica gel eluting with 50% AcOEt/Hexane

ORD record

ord-e38829eb64e348e38ddd3c72f10e5bc3

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728022B2