Methanol → HCID 67516356, compound

A mixture of (3-bromo-4-methylphenyl)(3,3-dimethyloxiran-2-yl)methanone (500 mg, 1.85 mmol, 1.0 eq) and hydroxylamine hydrochloride (500 mg, 7.19 mmol, 3.9 eq) in a 5:3 volumetric mixture of methanol and pyridine was heated at gentle reflux for 12 h. The resulting mixture was cooled to room temperature and the solvent was evaporated under vacuum. The residue was taken in water (10 mL) acidified with glacial acetic acid and stirred for 10 min. Ethyl acetate (50 mL) was added to the above mixture and the layers were separated. The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried (Na2SO4) and filtered. The filtrate was evaporated under vacuum to afford 320 mg of the desired product as a white solid. 1HNMR (400 MHz, CDCl3) δ 7.97 (d, J=1.0 Hz, 1H), 7.65 (dd, J=1.0, 8.0 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 4.78 (s, 1H), 2.42 (s, 3H), 1.51 (s, 3H), 1.31 (s, 3H); ESI-MS (m/z) 284, 286 [(MH)+, Br79,81].

1. temperaturewas heated
2. temperatureat gentle reflux for 12 h
3. customthe solvent was evaporated under vacuum
4. additionEthyl acetate (50 mL) was added to the above mixture
5. customthe layers were separated
6. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
7. washThe combined organic layers were washed with water (20 mL), brine (20 mL)
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. customThe filtrate was evaporated under vacuum

ORD record

ord-525888ae41614129873e7681a7c35ddd

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169242B2