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

HRID 229068

Reaktionsgleichung

Reaktionsgleichung von HRID 229068
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]=[C:30]([CH3:34])[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][CH:31]=[C:30]([CH3:34])[N:29]=2)=[N:22][C:23]([CH3:27])=[C:24]([CH3:26])[CH:25]=1

Komponenten

4

Edukt 2

HCID 6395Methanesulfonic AcidHCID 577565403-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,6'-trimethyl-[2,2']bipyridine2×

Produkt 1

HCID 1361316246-Methoxy-4-(5,6,6'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-olAusbeute 112,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

3-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,6′-trimethyl-[2,2′]bipyridine (compound 442) (475 mg) was dissolved in trifluoroacetic acid (4.7 ml) to prepare a solution. Methanesulfonic acid (0.47 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 (433 mg, yield 100%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4f1c58b8c7a14ae98d162f9daf01ad75
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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