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

HRID 1750086Notes

Reaction equation

HRID 1750086 reaction equation
[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

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 442032017-Hydroxy-3,4-dihydro-2H-isoquinolin-1-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9ae128d141b04e8fa73cde50c86406a2
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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