Water → 7-(2-Methoxyethoxy)-2,8-dimethylquinoline

HRID 338922Notes

Reaction equation

HRID 338922 reaction equation
Br[CH2:2][CH2:3][O:4][CH3:5].[CH3:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:10]([CH3:18])[C:11]([OH:17])=[CH:12][CH:13]=2)[N:8]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:5][O:4][CH2:3][CH2:2][O:17][C:11]1[C:10]([CH3:18])=[C:9]2[C:14]([CH:15]=[CH:16][C:7]([CH3:6])=[N:8]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 1357421682,8-Dimethylquinolin-7-ol

Product 1

HCID 709840567-(2-Methoxyethoxy)-2,8-dimethylquinolineYield 17%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromo-2-methoxyethane (0.64 g, 4.6 mmol), 2,8-dimethylquinolin-7-ol (1.0 g, 2.3 mmol) and potassium carbonate (0.96 g, 6.9 mmol) in acetone (15 mL) were heated to 70° C. in a sealed tube for 18 hours. After cooling, water (20 mL) was added and the aqueous phase was extracted with DCM. The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 7-(2-methoxyethoxy)-2,8-dimethylquinoline (90 mg, 17% yield) as an oil

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by reverse phase chromatography (SP4, 25M
  7. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-c053146f848b4500ac03e6a18b328418
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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