8-Hydroxyquinoline → 8-Methoxyquinoline

HRID 1972101Notes

Reaction equation

HRID 1972101 reaction equation
[OH-].[K+].[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.[CH3:14]I>C1COCC1>[CH3:14][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

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 6328Methyl iodideHCID 14797Potassium Hydroxide

Product 1

HCID 703108-MethoxyquinolineYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add potassium hydroxide (435 g, 7.76 mol) to a solution of 8-hydroxy quinoline (250 g, 1.724 mol) in THF (10 L) at ambient temperature and stir. Add methyl iodide (435 g, 2.58 mol) dropwise and stir overnight. Filter the reaction mixture and wash the solid with THF (2 L). Concentrate the solution to dryness; add water; extract with dichloromethane (2×3 L); combine the organic layers; and wash with brine. Collect the organic layers and dry over sodium sulfate. Remove the solids by filtration. Collect the filtrate and concentrate under reduced pressure to give a red oil, which solidifies on standing, to give the title compound (281 g, 102%), which can be used without further purification. ESI (m/z) 160(M+H).

Workup

  1. filtrationFilter the reaction mixture
  2. washwash the solid with THF (2 L)
  3. concentrationConcentrate the solution to dryness
  4. extractionextract with dichloromethane (2×3 L)
  5. washand wash with brine
  6. customCollect the organic layers
  7. dry with materialdry over sodium sulfate
  8. customRemove the solids
  9. filtrationby filtration
  10. customCollect the filtrate
  11. concentrationconcentrate under reduced pressure
  12. customto give a red oil, which

Sources & evidence

ORD record
ord-22aff9c0413e4861a47152c17d54eb12
Source dataset
uspto-grants-2013_04
Patent number
US08431706B2

Reaction notes

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