Methanesulfonic Acid → [2-(7-Hydroxy-6-methoxyquinolin-4-yloxy)-5-methoxyphenyl]ethanone
Reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[C:28](=[O:30])[CH3:29])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:31][CH3:32])C1C=CC=CC=1.CS(O)(=O)=O>FC(F)(F)C(O)=O>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[C:28](=[O:30])[CH3:29])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:31][CH3:32]Participants
Conditions
- Temperature
- 70 °C
Procedure
[2-(7-Benzyloxy-6-methoxyquinolin-4-yloxy)-5-methoxyphenyl]-ethanone (intermediate 3) (2.52 g) was suspended in a mixed solution composed of methanesulfonic acid (3.0 ml) and trifluoroacetic acid (50 ml), and the suspension was stirred at 70° C. for 0.5 hr. The solvent was removed therefrom by distillation under the reduced pressure. Water was added to the residue, and the mixture was neutralized with sodium hydrogencarbonate powder. The mixture was then extracted with chloroform. The chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give the title compound (1.23 g, yield 62%).
Workup
- customThe solvent was removed
- distillationby distillation under the reduced pressure
- additionWater was added to the residue
- extractionThe mixture was then extracted with chloroform
- washThe chloroform layer was then washed with water and saturated brine
- dry with materialwas dried over anhydrous sodium sulfate
- customThe solvent was removed
- distillationby distillation under the reduced pressure
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-b4a36f34e87f44cc820a39f1ca4e980a
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560558B2
Reaction notes
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