Water → 7-Bromo-2-(2-hydroxyethyl)-isoquinolin-1-one

HRID 2068593Notes

Reaction equation

HRID 2068593 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][OH:22].O>CN(C)C=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:20][CH2:21][OH:22])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 112761337-Bromoisoquinolin-1-ol

Product 1

HCID 592382027-Bromo-2-(2-hydroxyethyl)-isoquinolin-1-oneYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 5 (19.8 g, 88.4 mmol), potassium carbonate (18.3 g, 133 mmol) and 2-bromoethanol (13.3 g, 106 mmol) in dimethylforamide (200 mL) was stirred at 80° C. for 12 h. Then the mixture was cooled to room temperature and poured into water. The mixture was extracted with ethyl acetate (three times 500 mL), dried (sodium sulfate), concentrated and purified by chromatography on silica gel to give 6 (16.2 g, 68%)

Workup

  1. extractionThe mixture was extracted with ethyl acetate (three times 500 mL)
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated
  4. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-a2dd00f879784a5797fb0676e3ae4eac
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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