Hydroxyamine hydrochloride → HCID 73863353, compound

A suspension of 404 mg (1.39 mmol) of Compound 18, 290 mg (4.17 mmol) of hydroxylamine hydrochloride and 342 mg (4.17 mmol) of sodium acetate in 40 ml of methanol was refluxed for 22 hours. To the reaction mixture, 97 mg (1.39 mmol) of hydroxylamine hydrochloride and 114 mg (1.39 mmol) of sodium acetate were added, followed by further refluxing for 19 hours. The reaction mixture was concentrated under reduced pressure and a half-saturated aqueous solution of potassium carbonate was added to the residue. The thus-obtained mixture was extracted with chloroform (3 times). The organic layer was washed successively with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluent: chloroform), whereby 338 mg of the title compound were obtained (yield: 80%).

1. temperaturewas refluxed for 22 hours
2. temperatureby further refluxing for 19 hours
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. additiona half-saturated aqueous solution of potassium carbonate was added to the residue
5. extractionThe thus-obtained mixture was extracted with chloroform (3 times)
6. washThe organic layer was washed successively with water
7. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by chromatography on a silica gel column (eluent: chloroform)

ORD record

ord-cb0c2a9e74ce4405a436c79d4bbbb29f

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06624314B2