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Chloride → 1-{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methoxyphenyl}-1-propanone

HRID 228570
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228570
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[CH:24]([OH:27])[CH2:25][CH3:26].C1CCN2C(=NCCC2)CC1.[Cl-].O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:24](=[O:27])[CH2:25][CH3:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 312ChlorideHCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 577565241-{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methoxyphenyl}-1-propanol2×

Produkt 1

HCID 248791481-{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methoxyphenyl}-1-propanoneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Under an argon atmosphere, 1-{2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-methoxyphenyl}-1-propanol (compound 11) (65.9 mg) was dissolved in methylene chloride (2 ml) to prepare a solution. 1,8-Diazabicyclo[5.4.0]-7-undecene (72 mg) was then added to the solution, and the mixture was cooled to −78° C. N-Tert-butylbenzenesulfineimidoyl chloride (71.4 mg) was dissolved in methylene chloride to prepare a solution, and the solution was added to the reaction solution. The mixture was stirred at −78° C. for 30 min and at 0° C. for 30 min. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-hexane to give the title compound (56.2 mg, yield 86%).

Aufarbeitung

  1. customto prepare a solution
  2. customto prepare a solution
  3. additionthe solution was added to the reaction solution
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was then washed with saturated brine
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customThe solvent was removed
  8. distillationby distillation under the reduced pressure
  9. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b5999b59cce14d5f82336b42d9fa5085
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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