Methanesulfonic Acid → HCID 57756597, compound

HRID 228700Notes

Reaction equation

HRID 228700 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][CH:20]=2)=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)C1C=CC=CC=1.CS(O)(=O)=O.FC(F)(F)C(O)=O>>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][C:25]=1[O:31][CH3:32])[N:22]=[CH:21][CH:20]=[C:19]2[O:18][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][C:13]=1[C:15](=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 6422Trifluoroacetic acidHCID 57756346HCID 57756346, compound2×

Product 1

HCID 57756597HCID 57756597, compoundYield 100%

Conditions

Temperature
70 °C

Procedure

1-[5-Benzyloxy-2-(6,7-dimethoxy-quinolin-4-yloxy)-phenyl]-ethanone (compound 175) (188 mg) was suspended in a mixed solution composed of methanesulfonic acid (0.3 ml) and trifluoroacetic acid (4 ml) to prepare a suspension which was then stirred at 70° C. for 1.5 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. 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. The residue was purified by column chromatography using acetone-hexane to give the title compound (145 mg, yield 100%).

Workup

  1. customto prepare a suspension which
  2. customThe solvent was removed by distillation under the reduced pressure, water
  3. additionwas added to the residue
  4. extractionwas then extracted with chloroform
  5. washThe chloroform layer was then washed with water and saturated brine
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-eebba6a5fe2a4725982159c18b6c1ca8
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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