4-Methoxyphenol → HCID 22132780, compound

HRID 1857109Notes

Reaction equation

HRID 1857109 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][C:21]([OH:24])=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[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:21]1[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 22132780HCID 22132780, compoundYield 1,541.4%

Reagents, catalysts & solvents 1

HCID 21584013Chloroform ethylacetateSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (103 mg) and commercially available 4-methoxyphenol (286 mg) were mixed and stirred at 150° C. for 6 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 dried with anhydrous 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/ethyl acetate to obtain 2.21 g of the title compound (yield: 88%).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washthe ethyl acetate layer was washed with brine
  3. dry with materialdried with anhydrous 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-d20ab702e75d43feb19d7e21baf4616f
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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