Hydrochloric Acid → 6-Bromo-2-(4-methanesulfonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehyde

HRID 750267ノート

反応式

HRID 750267 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[C:6]([CH2:24][OH:25])=[C:5]2[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C.O.Cl>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:18][CH:19]=1)[C:6]([CH:24]=[O:25])=[C:5]2[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 230608406-bromo-3-hydroxymethyl-2-(4-methanesulfonylbenzyl)-4-phenyl-2H-isoquinolin-1-one

生成物 1

HCID 230608166-Bromo-2-(4-methanesulfonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehyde収率 94.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 6-bromo-3-hydroxymethyl-2-(4-methanesulfonylbenzyl)-4-phenyl-2H-isoquinolin-1-one (1.0 g) in DMSO (10 ml) was added triethylamine (4.4 ml), and pyridine sulfur trioxide complex (2.6 g) was added at room temperature, and the mixture was stirred for 1 hr. and the reaction mixture was added to water. 10% Hydrochloric acid was added to acidify the aqueous layer and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from diisopropyl ether to give the title compound (940 mg).

後処理

  1. additionwas added at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was crystallized from diisopropyl ether

出典と根拠

ORDレコード
ord-4ed9c3368a364e1187500fb2c48ccd6f
出典データセット
uspto-grants-2008_07
特許番号
US07402595B2

反応ノート

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