1,3-Dibromopropane → 7-(3-bromopropoxy)-3,4-dihydroisoquinolin-1(2H)-one

HRID 1750086ノート

反応式

HRID 1750086 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]Br.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Br:13][CH2:14][CH2:15][CH2:16][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 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 442032017-Hydroxy-3,4-dihydro-2H-isoquinolin-1-one

生成物 1

HCID 666321077-(3-bromopropoxy)-3,4-dihydroisoquinolin-1(2H)-one収率 63.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of intermediate 19 (326 mg, 2 mmol), 1,3-dibromopropane (0.62 mL, 6 mmol) and anhydrous K2CO3 (276 mg, 2 mmol) was dissolved in 4 mL of EtOH 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=5:1) to give 7-(3-bromopropoxy)-3,4-dihydroisoquinolin-1(2H)-one (intermediate 20) (360 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=5:1)

出典と根拠

ORDレコード
ord-9ae128d141b04e8fa73cde50c86406a2
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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