Methyl iodide → 3,8-Dimethoxy quinoline

HRID 399745Notes

Reaction equation

HRID 399745 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[O:12][CH3:13].[OH-].[K+].I[CH3:17]>C(O)C>[CH3:17][O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[O:12][CH3:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 110843893-Quinolinol, 8-methoxy-2×

Product 1

HCID 105837983,8-Dimethoxy quinolineYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

175 mg of 3-hydroxy-8-methoxy quinoline [compound (V)] prepared in example 6 and 66 mg of potassium hydroxide were added to 3 ml of ethanol, and the solution was agitated for 30 minutes. To the solution was added 284 mg of iodomethane, and the solution was agitated for 24 hours. The solvent was removed, and the solution was extracted with dichloromethane. The dichloromethane layer was washed with water and aqueous sodium hydroxide, and dried with anhydrous magnesium sulfate. The dichloromethane was removed by vacuum distillation to give 165 mg of 3,8-dimethoxy quinoline.

Workup

  1. stirringthe solution was agitated for 24 hours
  2. customThe solvent was removed
  3. extractionthe solution was extracted with dichloromethane
  4. washThe dichloromethane layer was washed with water and aqueous sodium hydroxide
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe dichloromethane was removed by vacuum distillation

Sources & evidence

ORD record
ord-aaf958ebc6be4ebdac4f38df1b6371fc
Source dataset
uspto-grants-1998_10
Patent number
US05824689

Reaction notes

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