1,4-Dibromobutane → 7-(4-Bromobutoxy)-3,4-dihydro-1(2h)-isoquinolinone

HRID 1750088ノート

反応式

HRID 1750088 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 442032017-Hydroxy-3,4-dihydro-2H-isoquinolin-1-one

生成物 1

HCID 686269787-(4-Bromobutoxy)-3,4-dihydro-1(2h)-isoquinolinone収率 64.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of intermediate 19 (196 mg, 1.2 mmol), 1,4-dibromobutane (0.43 mL, 3.6 mmol) and anhydrous K2CO3 (166 mg, 1.22 mmol) was dissolved in EtOH (4 mL) and the solution was heated to reflux and stirred overnight. The mixture was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with water, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE/EtOAc=3:1) to give 7-(4-bromobutoxy)-3,4-dihydroisoquinolin-1(2H)-one (intermediate 21) (230 mg, 63%) as a white solid.

後処理

  1. temperaturethe solution was heated
  2. temperatureto reflux
  3. extractionextracted with EtOAc
  4. washThe combined EtOAc layers were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel column (elution with PE/EtOAc=3:1)

出典と根拠

ORDレコード
ord-665f2fe296d7444ea6ad63db60b97c7a
出典データセット
uspto-grants-2015_10
特許番号
US09156822B2

反応ノート

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