4-Chloro-6,7-dimethoxyquinoline → HCID 22132800, compound

HRID 1857110Notes

Reaction equation

HRID 1857110 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.[OH:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[N:22]2.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:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[N:22]2

Participants

5

Reactant 3

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium BicarbonateHCID 135441757Quinolin-5-ol

Product 1

HCID 22132800HCID 22132800, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
170 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (50 mg) and commercially available 5-hydroxyquinoline (50 mg) were mixed and stirred at 170° C. for 10 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 thin layer chromatography on silica gel eluting first with hexane/ethyl acetate (1/1) and then with chloroform/methanol (50/1) to obtain 47 mg of the title compound (yield: 64%).

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 thin layer chromatography on silica gel eluting first with hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-46e6af471b124960a9385b35535cbb55
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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