Hydroxyamine hydrochloride → HCID 53945844, compound

HRID 1417560Notes

Reaction equation

HRID 1417560 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]([C:14](=O)[CH3:15])[C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[NH2:18]O>C(O)C.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([CH3:15])=[N:18][O:13][C:11]=2[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 54261822HCID 54261822, compound

Product 1

HCID 53945844HCID 53945844, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-(3-bromo-4-methoxyphenyl)pentane-2,4-dione (40 mg, 0.14 mmol) and hydroxylamine hydrochloride (30 mg, 0.43 mmol) in 95% ethanol (0.50 mL) was refluxed for 4 h. After cooling to RT, the mixture was taken up in 30 mL of ether and washed with 10 mL of saturated sodium bicarbonate solution followed by 10 mL of brine. Drying over sodium sulfate and concentration afforded 40 mg of crude product which was purified by flash column chromatography, eluting with 50% dichloromethane in hexane, to yield 28 mg of the title compound as a white solid. Mass spectrum (NH3/CI): m/z=282 (M+1).

Workup

  1. temperaturewas refluxed for 4 h
  2. washwashed with 10 mL of saturated sodium bicarbonate solution
  3. dry with materialDrying over sodium sulfate and concentration
  4. customafforded 40 mg of crude product which
  5. customwas purified by flash column chromatography
  6. washeluting with 50% dichloromethane in hexane

Sources & evidence

ORD record
ord-0dbef16296574f8b945bd497cb7e71a3
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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