Methanesulfonic Acid → 7-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-6-ol

HRID 229019Notes

Reaction equation

HRID 229019 reaction equation
FC(F)(F)C(O)=O.CS(O)(=O)=O.C([O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[N:27]=[CH:26][CH:25]=[C:24]2[O:33][C:34]1[C:35]([CH3:44])=[N:36][C:37]2[C:42]([CH:43]=1)=[CH:41][CH:40]=[CH:39][CH:38]=2)C1C=CC=CC=1>>[CH3:32][O:31][C:30]1[CH:29]=[C:28]2[C:23]([C:24]([O:33][C:34]3[C:35]([CH3:44])=[N:36][C:37]4[C:42]([CH:43]=3)=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:25][CH:26]=[N:27]2)=[CH:22][C:21]=1[OH:20]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 6422Trifluoroacetic acidHCID 230784416-Benzyloxy-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline2×

Product 1

HCID 230782657-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-6-olYield 5%

Conditions

Temperature
100 °C

Procedure

Trifluoroacetic acid (5 ml) and methanesulfonic acid (0.2 ml) were added to 6-benzyloxy-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline (compound 415) (700 mg), and the mixture was stirred at 100° C. for 2 hr. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. A saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with a saturated aqueous sodium hydrogencarbonate solution and water and was then 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 7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-6-ol (26 mg, yield 5%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was then removed by distillation under the reduced pressure
  3. additionA saturated aqueous sodium hydrogencarbonate solution was added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with a saturated aqueous sodium hydrogencarbonate solution and water
  6. dry with materialwas then 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-0de9d93563324f5f83802546bc109ec9
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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