Methanesulfonic Acid → 4-(5,6-Dimethyl-2-phenyl-pyridin-3-yloxy)-6-methoxy-quinolin-7-ol

HRID 228932Notes

Reaction equation

HRID 228932 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[C:21]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[N:22][C:23]([CH3:27])=[C:24]([CH3:26])[CH:25]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:34][CH3:35])C1C=CC=CC=1.CS(O)(=O)=O>FC(F)(F)C(O)=O>[CH3:26][C:24]1[CH:25]=[C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:34][CH3:35])[CH:11]=3)[N:16]=[CH:15][CH:14]=2)[C:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[N:22][C:23]=1[CH3:27]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 230783827-Benzyloxy-4-(5,6-dimethyl-2-phenyl-pyridin-3-yloxy)-6-methoxy-quinoline2×

Product 1

HCID 1358548394-(5,6-Dimethyl-2-phenyl-pyridin-3-yloxy)-6-methoxy-quinolin-7-olYield 109.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

7-Benzyloxy-4-(5,6-dimethyl-2-phenyl-pyridin-3-yloxy)-6-methoxy-quinoline (compound 331) (958 mg) was dissolved in trifluoroacetic acid (9.5 ml) to prepare a solution. Methanesulfonic acid (0.95 ml) was added to the solution, and the mixture was stirred at 70° C. for one hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. An aqueous sodium hydrogencarbonate solution was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with saturated brine and was dried over anhydrous sodium 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 (848 mg, yield 100%).

Workup

  1. customto prepare a solution
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was removed by distillation under the reduced pressure
  4. additionAn aqueous sodium hydrogencarbonate solution was then added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe chloroform layer was washed with saturated brine
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-16ae57d124bc49268996b5f3e1bd0282
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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