4-Chloro-6,7-dimethoxyquinoline → (4-n-Butylphenyl){4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanone
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][CH:22]=1>COCCOCCOC>[CH2:16]([C:13]1[CH:12]=[CH:11][C:10]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][C:21]3[C:30]4[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=4)[N:24]=[CH:23][CH:22]=3)=[CH:7][CH:6]=2)=[O:9])=[CH:15][CH:14]=1)[CH2:17][CH2:18][CH3:19]Participants
Conditions
- Temperature
- 180 °C
Procedure
Under argon, 4-n-butylphenyl 4-hydroxyphenyl ketone (727 mg) obtained in Example 148 and 4-chloro-6,7-dimethoxyquinoline (639 mg) were dissolved in diethylene glycol dimethyl ether (10 ml), and the solution was then refluxed with heat at 180° C. for 10 hours. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was then dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate and then with chloroform, followed by chromatography on silica gel eluting with hexane/acetone to obtain 400 mg of the title compound (yield: 32%).
Workup
- temperaturethe solution was then refluxed
- customThe reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform
- dry with materialthe chloroform layer was then dried with anhydrous magnesium sulfate
- customAfter removing the solvent
- distillationby reduced-pressure distillation
- customthe resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-cd8b2f961fa845ceb70777c3bb0c6ae8
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06143764
Reaction notes
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