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Dimethyl Sulfoxide → 2-Benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehyde

HRID 750263
ノート
印刷プレビュー

反応式

HRID 750263 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[C:27]([CH2:28][OH:29])=[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Br:36])[CH:24]=2)[C:19]1=[O:37])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C1COCC1.O>[CH2:11]([N:18]1[C:27]([CH:28]=[O:29])=[C:26]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Br:36])[CH:24]=2)[C:19]1=[O:37])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 230609532-benzyl-6-bromo-3-hydroxymethyl-4-phenyl-2H-isoquinolin-1-one

生成物 1

HCID 230605422-Benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehyde収率 62.6%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Under a nitrogen stream, to a solution of oxalyl chloride (0.54 ml) in THF (28 ml) was added dropwise a solution of DMSO (0.58 ml) in THF (5 ml) at −70° C. or below and the mixture was stirred for 10 min. A solution of 2-benzyl-6-bromo-3-hydroxymethyl-4-phenyl-2H-isoquinolin-1-one (1.30 g) in THF (7 ml) was added dropwise at −70° C. or below and the mixture was stirred at −60° C. to −50° C. for 1 hr. To the reaction mixture was added dropwise triethylamine (3.1 ml) at 50° C. or below and the mixture was allowed to warm to room temperature and stirred for 30 min. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from ethyl acetate-hexane to give the title compound (810 mg).

後処理

  1. stirringthe mixture was stirred at −60° C. to −50° C. for 1 hr
  2. stirringstirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was crystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-db44c299562f4bea80090e95d41dd899
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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