Methanesulfonic Acid → HCID 136131617, compound

HRID 228909Notes

Reaction equation

C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([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]=[C:24]([CH3:26])[C:23]([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)-4,5-dimethyl-phenyl]-ethanone (compound 313) (1.10 g) was suspended in a mixed solution composed of methanesulfonic acid (0.8 ml) and trifluoroacetic acid (10 ml), and the mixture was stirred at 70° C. for one hr. 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. Next, the chloroform layer was 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 (700 mg, yield 83%).

Workup

customThe solvent was removed by distillation under the reduced pressure, water
additionwas added to the residue
extractionwas then extracted with chloroform
washNext, the chloroform layer was 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-cd74f7b57e65490584df2210786a7b67
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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