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Dimethylformamide → 6-Bromo-2-(2-hydroxy-2-methylpropyl)isoquinolin-1(2H)-one

HRID 601686
ノート
印刷プレビュー

反応式

HRID 601686 の反応式
[H-].[Na+].CN(C)C=[O:6].[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][CH:13]=[CH:12]2.Br[CH2:21][C:22]([CH3:24])=[CH2:23]>O>[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:21][C:22]([OH:6])([CH3:24])[CH3:23])[CH:13]=[CH:12]2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 3577853-Bromo-2-methyl-1-propeneHCID 158851826-Bromoisoquinolin-1(2H)-one

生成物 1

HCID 231581986-Bromo-2-(2-hydroxy-2-methylpropyl)isoquinolin-1(2H)-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Under nitrogen atmosphere, 23 mg of 60% of sodium hydride was added at 0° C. to 2 ml solution of dimethylformamide with 62 mg of 6-bromo-2H-isoquinoline-1-one, and the mixture was stirred for 30 30 min. Then, 0.055 ml of 3-bromo-2-methyl-propene was added at 0° C., and the mixture was stirred at room temperature for 2 hours. Cold water was added to the reaction solution, extracted with chloroform. Chloroform layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by thin-layer chromatography (hexane/ethyl acetate=3/1). The obtained compounds were dissolved in concentrated hydrochloric acid, stirred at 100° C. for 3 hours, and then cooled down to room temperature. After making it alkaline with 50% sodium hydride aqueous solution, the mixture was stirred at room temperature for 3 hours. Cold water was added to the reaction solution, and extracted with chloroform. Chloroform layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by thin-layer chromatography (hexane/ethyl acetate=3/1) to obtain 20 mg of the above compound as a white solid.

後処理

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionextracted with chloroform
  3. washChloroform layer was washed with saturated saline solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationThe solvents were distilled outunder reduced pressure
  6. customthe residues were separated
  7. custompurified by thin-layer chromatography (hexane/ethyl acetate=3/1)
  8. dissolutionThe obtained compounds were dissolved in concentrated hydrochloric acid
  9. stirringstirred at 100° C. for 3 hours
  10. stirringthe mixture was stirred at room temperature for 3 hours
  11. additionCold water was added to the reaction solution
  12. extractionextracted with chloroform
  13. washChloroform layer was washed with saturated saline solution
  14. dry with materialdried with anhydrous sodium sulfate
  15. distillationThe solvents were distilled outunder reduced pressure
  16. customthe residues were separated
  17. custompurified by thin-layer chromatography (hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-40bdf9ebdec94a74b5328ea93bc6fbc1
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902369B2

反応ノート

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