Hydroxyamine hydrochloride → 3-acetyl-6-bromo-2-[4-(1-hydroxyiminoethyl)benzyl]-4-phenyl-2H-isoquinolin-1-one

HRID 750318Notes

Reaction equation

HRID 750318 reaction equation
[C:1]([C:4]1[N:5]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=O)[CH3:30])=[CH:25][CH:24]=2)[C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][C:10]([Br:20])=[CH:9][CH:8]=2)(=[O:3])[CH3:2].Cl.[NH2:33][OH:34].C([O-])(=O)C.[Na+]>C(O)C>[C:1]([C:4]1[N:5]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29](=[N:33][OH:34])[CH3:30])=[CH:27][CH:28]=2)[C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][C:10]([Br:20])=[CH:9][CH:8]=2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 230609443-acetyl-2-(4-acetylbenzyl)-6-bromo-4-phenyl-2H-isoquinolin-1-one

Product 1

HCID 865995673-acetyl-6-bromo-2-[4-(1-hydroxyiminoethyl)benzyl]-4-phenyl-2H-isoquinolin-1-oneYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-acetyl-2-(4-acetylbenzyl)-6-bromo-4-phenyl-2H-isoquinolin-1-one (95 mg) in ethanol (10 ml) were added hydroxylamine hydrochloride (17 mg) and sodium acetate (29 mg) at room temperature and the mixture was heated under reflux for 6 hrs. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution, washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1→3/2) to give the title compound (84 mg, 86%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hrs
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  5. washwashed with saturated brine
  6. customdried
  7. additionby adding sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1→3/2)

Sources & evidence

ORD record
ord-27afc23ba119415da0334e4b1e3d64db
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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