Pyridine → HCID 86641936, compound

1-(5-Bromo-2-cyclopentyloxyphenyl)ethanone (5.0 g, 17.65 mmol) was dissolved in a mixed solvent of chloroform (18 ml) and methanol (70 ml). Hydroxylamine hydrochloride (1.88 g, 27.0 mmol) and pyridine (4.36 ml, 54.1 mmol) were added to the resulting solution, and the mixture was stirred for 6 hours while heating under reflux. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. 2N Hydrochloric acid (13.9 ml) was added to the residue, and the resulting mixture was extracted with dichloromethane. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was washed with n-hexane and dried to thereby obtain 4.6 g of powdery white 1-(5-bromo-2-cyclopentyloxyphenyl)ethanone oxime (yield: 87%).

1. temperaturewhile heating
2. temperatureunder reflux
3. concentrationconcentrated under reduced pressure
4. addition2N Hydrochloric acid (13.9 ml) was added to the residue
5. extractionthe resulting mixture was extracted with dichloromethane
6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated to dryness under reduced pressure
9. washThe residue was washed with n-hexane
10. customdried

ORD record

ord-4bcb83e441ca4f82b5c3e15d940e17bc

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045464B2