8-Hydroxyquinoline → 8-allyloxyquinoline

HRID 495423Notes

Reaction equation

HRID 495423 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2.[CH2:14](Br)[CH:15]=[CH2:16]>CN(C=O)C>[CH2:16]([O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 7841Allyl bromideHCID 24758Sodium hydride

Product 1

HCID 4613598-allyloxyquinolineYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% oil dispersion, 3.0 g, 75 mmol) in DMF (100 mL) at 0° C. under argon, was added a solution of 8-hydroxyquinoline (9.2 g, 64 mmol) in DMF (20 mL) dropwise. The mixture was allowed to stir for 0.5 h, then allyl bromide (6.6 mL, 77 mmol) was added dropwise. The mixture was stirred at room temperature for 20 h, then was poured into ice/water (400 mL) and extracted with ether (3×300 mL). Combined organic extracts were washed with water (500 mL) and evaporated in vacuo. The crude residue was purified by silica gel chromatography (ethyl acetate in hexane 25%-75% gradient) to give 8-allyloxyquinoline (8.5 g, 72%) as an oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 h
  2. extractionextracted with ether (3×300 mL)
  3. washCombined organic extracts were washed with water (500 mL)
  4. customevaporated in vacuo
  5. customThe crude residue was purified by silica gel chromatography (ethyl acetate in hexane 25%-75% gradient)

Sources & evidence

ORD record
ord-ba6fc45f0ca14819b446dac12332dc5a
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

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