1-Naphthol → HCID 22132790, compound

HRID 1857111Notes

Reaction equation

HRID 1857111 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:16]1([OH:26])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.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:26][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 70051-NaphtholHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 22132790HCID 22132790, compoundYield 40%

Conditions

Temperature
150 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (97 mg) and commercially available 1-naphthol (340 mg) 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 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 (3/1) and then with chloroform/methanol (100/1), and further purified by thin layer chromatography on silica gel eluting with hexane/ethyl acetate (1/1) to obtain 57 mg of the title compound (yield: 40%).

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 (3/1)
  7. customwith chloroform/methanol (100/1), and further purified by thin layer chromatography on silica gel eluting with hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-575786797e5f462492297a4cf62650f9
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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