Methanesulfonic Acid → 6-Methoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-ol

HRID 229078Notes

Reaction equation

HRID 229078 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][C:31]([CH3:34])=[CH:30][N: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:35][CH3:36])C1C=CC=CC=1.CS(O)(=O)=O>FC(F)(F)C(O)=O>[CH3:36][O:35][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[O:19][C:20]1[C:21]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][N:29]=2)=[N:22][C:23]([CH3:27])=[C:24]([CH3:26])[CH:25]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 577563763-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,5'-trimethyl-[2,2']bipyridine2×

Product 1

HCID 1361316196-Methoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-olYield 88.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

3-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,5′-trimethyl-[2,2′]bipyridine (compound 452) (500 mg) was dissolved in trifluoroacetic acid (5 ml) to prepare a solution. Methanesulfonic acid (0.5 ml) was added to the solution, and the mixture was stirred at 70° C. for 1.5 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 thin layer chromatography using chloroform-methanol to give the title compound (358 mg, yield 88%).

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 thin layer chromatography

Sources & evidence

ORD record
ord-2b7743f2952646a7b420c0f6ad91d9fd
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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