Acetylresorcinol → 3-(6,7-Dimethoxy-quinolin-4-yloxy)-phenol

HRID 1857105Notes

Reaction equation

HRID 1857105 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.C([O:19][C:20]1[CH:26]=[CH:25][CH:24]=[C:22]([OH:23])[CH:21]=1)(=O)C.C(=O)([O-])O.[Na+]>>[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:19][C:20]1[CH:26]=[CH:25][CH:24]=[C:22]([OH:23])[CH:21]=1

Participants

4

Reactant 3

HCID 5055AcetylresorcinolHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 226465273-(6,7-Dimethoxy-quinolin-4-yloxy)-phenolYield 9%

Conditions

Temperature
180 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (300 mg) and commercially available resorcinol monoacetate (0.835 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 crystallized with chloroform to obtain 37 mg of the title compound (yield: 9%).

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 crystallized with chloroform

Sources & evidence

ORD record
ord-4432125e71764daeb1697b6327f5d441
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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