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Water → 1-{3-[7-(2,3-Dihydroxy-propoxy)-6-methoxy-quinolin-4-yloxy]-quinolin-2-yl}-ethanone

HRID 228997
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228997
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14]C1CO1)[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[C:20]([C:29](=[O:31])[CH3:30])=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.F[C:33](F)(F)[C:34]([OH:36])=O.[OH-:39].[Na+].O>C(Cl)Cl>[OH:39][CH:33]([CH2:34][OH:36])[CH2:14][O:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([O:18][C:19]3[C:20]([C:29](=[O:31])[CH3:30])=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:2][CH3:1]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 577565081-[3-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-quinolin-2-yl]-ethanone2×

Produkt 1

HCID 577564701-{3-[7-(2,3-Dihydroxy-propoxy)-6-methoxy-quinolin-4-yloxy]-quinolin-2-yl}-ethanoneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-[3-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-quinolin-2-yl]-ethanone (compound 394) (150 mg) was dissolved in methylene chloride (2 ml) to prepare a solution which was brought to 0° C. Trifluoroacetic acid (1 ml) was added to the solution, and the mixture was stirred at 0° C. for 30 min. The mixture was then stirred at room temperature for 4 hr. The reaction solution was brought to 0° C. and was stirred. The reaction solution was made alkaline by the addition of a 10% aqueous sodium hydroxide solution. Water was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then 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 (140 mg, yield 90%).

Aufarbeitung

  1. customto prepare a solution which
  2. customwas brought to 0° C
  3. stirringThe mixture was then stirred at room temperature for 4 hr
  4. customwas brought to 0° C.
  5. stirringwas stirred
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was then washed with saturated brine
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation under the reduced pressure
  10. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-625c838421ad491893e949910710dd16
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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