Guaiacol → 6,7-Dimethoxy-4-(2-methoxyphenoxy)quinoline

HRID 1857107Notes

Reaction equation

HRID 1857107 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[OH:24].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CO>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[O:17][CH3:16]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 221327636,7-Dimethoxy-4-(2-methoxyphenoxy)quinolineYield 54%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (102 mg) and commercially available 2-methoxyphenol (0.5 ml) were mixed and stirred at 150° C. for 8 hours. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate and then partitioned between water and ethyl acetate, and the ethyl acetate layer was washed with brine and then dried with sodium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by column chromatography on silica gel eluting first with hexane/ethyl acetate and then with chloroform/methanol to obtain 76 mg of the title compound (yield: 54%).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washthe ethyl acetate layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. customAfter removing the solvent
  5. distillationby reduced-pressure distillation
  6. customthe resulting residue was purified by column chromatography on silica gel eluting first with hexane/ethyl acetate

Sources & evidence

ORD record
ord-6ddfde449e1f4aa99c65ddec369bf1f1
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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