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

HRID 750318
ノート
印刷プレビュー

反応式

HRID 750318 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-27afc23ba119415da0334e4b1e3d64db
出典データセット
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07402595B2

反応ノート

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