Dimethyl Sulfoxide → 3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline
Reaction equation
[H-].[Na+].CS(C)=O.[ClH:7].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1Cl.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][CH:19]=1>O>[Cl:7][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:15][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][CH:19]=1)[NH2:8]Participants
Conditions
- Temperature
- 50 °C
Procedure
Sodium hydride (60 wt %, 0.72 g) was added to dimethyl sulfoxide (10 ml), and the mixture was stirred at 50° C. for 20 min. 4-Amino-3-chlorophenol hydrochloride (1.61 g) was added thereto, and the mixture was stirred at room temperature for 10 min. Next, 4-chloro-6,7-dimethoxyquinoline (1.00 g) was added thereto, and the mixture was stirred at 100° C. overnight. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. Methanol was added to the residue, and the precipitated crystal was collected by suction filtration to give the title compound (0.80 g, yield 60%).
Workup
- stirringthe mixture was stirred at room temperature for 10 min
- stirringthe mixture was stirred at 100° C. overnight
- extractionthe mixture was extracted with chloroform
- washThe chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution
- dry with materialwas dried over anhydrous sodium sulfate
- customThe solvent was removed by distillation under the reduced pressure
- additionMethanol was added to the residue
- filtrationthe precipitated crystal was collected by suction filtration
Sources & evidence
- ORD record
- ord-45ef327ffaeb41a3bf8e0dfbbe2d4707
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07135466B2
Reaction notes
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