3-Fluorophenol → HCID 22132626, compound

HRID 1857104Notes

Reaction equation

HRID 1857104 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.[F:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[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:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([F:16])[CH:18]=1

Participants

5

Reactant 3

HCID 97433-FluorophenolHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 22132626HCID 22132626, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (100 mg) and commercially available 3-fluorophenol (0.20 ml) were mixed and stirred at 180° C. for 30 minutes. 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 anhydrous sodium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate and then with chloroform to obtain 125 mg of the title compound (yield: 94%).

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 with hexane/ethyl acetate

Sources & evidence

ORD record
ord-6a3787a3eadc4633baa20a7486bac3dc
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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