Methanesulfonic Acid → [2-(7-Hydroxy-6-methoxyquinolin-4-yloxy)-5-methoxyphenyl]ethanone

HRID 228907Notes

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

1-[2-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5-methoxy-phenyl]-ethanone (2.52 g) was suspended in a mixed solution composed of methanesulfonic acid (3 ml) and trifluoroacetic acid (50 ml), and the suspension was stirred at 70° C. for 30 min. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the mixture was neutralized with sodium hydrogencarbonate powder and was then extracted with chloroform. The chloroform layer was then washed with water and saturated brine and was dried over anhydrous magnesium sulfate, the solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform-methanol to give the title compound (1.23 g, yield 62%).

Workup

customThe solvent was removed by distillation under the reduced pressure, water
additionwas added to the residue
extractionwas then extracted with chloroform
washThe chloroform layer was then washed with water and saturated brine
dry with materialwas dried over anhydrous magnesium sulfate
customthe solvent was removed by distillation under the reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-03b9325da3984268aef417a9ecd90cb2
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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