Allyl bromide → 1-Chloro-7-(2-propen-1-yloxy)isoquinoline

HRID 2060369Notes

Reaction equation

HRID 2060369 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[CH:20]=[CH2:21]>C(#N)C.OS([O-])(=O)=O.[K+].CCOC(C)=O>[CH2:21]([O:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][N:3]=[C:2]2[Cl:1])=[CH:7][CH:8]=1)[CH:20]=[CH2:19]

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 468354151-Chloroisoquinolin-7-ol

Product 1

HCID 581283311-Chloro-7-(2-propen-1-yloxy)isoquinolineYield 19%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516920Potassium bisulfateSolvent

Procedure

1-Chloroisoquinolin-7-ol (4.87 gm, 20.34 mmol) and cesium carbonate (6.63 g, 20.34 mmol) were combined in acetonitrile (100 mL) and stirred for 2 min. Allyl bromide (1.76 mL, 20.34 mmol) was added and the reaction mixture stirred for 30 min. The reaction mixture was diluted with aqueous KHSO4 (40 mL) and EtOAc (100 mL) and stirred. The organic extract was removed, dried over Na2SO4, concentrated and chromatographed on silica gel using 20-50% EtOAc/hexanes to give 0.85 g of an oil which solidified upon storing in the freezer. LRMS (M+H)+=220.1.

Workup

  1. stirringthe reaction mixture stirred for 30 min
  2. stirringstirred
  3. extractionThe organic extract
  4. customwas removed
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customchromatographed on silica gel using 20-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-3e8df870f33547df9e4e03b85ffe8f90
Source dataset
uspto-grants-2012_10
Patent number
US08278322B2

Reaction notes

Loading…