Allyl bromide → HCID 21107330, compound

HRID 1765546Notes

Reaction equation

HRID 1765546 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2.[CH2:14](Br)[CH:15]=[CH2:16]>CN(C)C=O>[CH2:16]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 113746-HydroxyquinolineHCID 24758Sodium hydride

Product 1

HCID 21107330HCID 21107330, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.33 g, 8.3 mmol) in anhydrous N,N-dimethylformamide (30 ml) was added 6-hydroxyquinoline (1.0 g, 6.9 mmol) at room temperature. The reaction mixture was stirred for 1 hour, then allyl bromide (0.72 ml, 8.3 mmol) was added. The reaction mixture was allowed to stir for 1 hour at room temperature, quenched with water and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum. Chromatography (50% hexanes-ethyl acetate) afforded 1.14 g (89%) of 6-allyloxyquinoline as brown oil. MS ESI m/z 185 [M+H]+.

Workup

  1. stirringto stir for 1 hour at room temperature
  2. customquenched with water
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-274288f136b145bda3829e948eb73818
Source dataset
uspto-grants-2007_06
Patent number
US07227023B2

Reaction notes

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