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Water → 1-(2-methylpropyl)-2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1H-imidazo[4,5-c]quinoline

HRID 599453
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 599453
O.[OH-].[Na+].[CH3:4][CH:5]([CH3:29])[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[NH:18][C:19](=O)[CH2:20][CH2:21][C:22]1([CH3:27])[O:26][CH2:25][CH2:24][O:23]1>C(O)C>[CH3:4][CH:5]([CH3:29])[CH2:6][N:7]1[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=[C:19]1[CH2:20][CH2:21][C:22]1([CH3:27])[O:26][CH2:25][CH2:24][O:23]1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67052427N-{4-[(2-methylpropyl)amino]quinolin-3-yl}-3-(2-methyl-1,3-dioxolan-2-yl)propanamide

Produkt 1

HCID 670523821-(2-methylpropyl)-2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1H-imidazo[4,5-c]quinolineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702Ethanol
Lösungsmittel

Versuchsvorschrift

Water (3 mL) followed by solid sodium hydroxide (0.4 g, 10.7 mmol) were added to a stirred solution of N-{4-[(2-methylpropyl)amino]quinolin-3-yl}-3-(2-methyl-1,3-dioxolan-2-yl)propanamide (2.55 g, 7.13 mmol) in ethanol (10 mL). The reaction mixture was heated at reflux for 30 minutes, then was allowed to cool to room temperature and was concentrated under reduced pressure. The resulting aqueous slurry was diluted with water (50 mL) and was extracted with dichloromethane (2×50 mL). The organic layers were combined, washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 2.3 g of crude 1-(2-methylpropyl)-2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1H-imidazo[4,5-c]quinoline as a clear oil.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 30 minutes
  3. concentrationwas concentrated under reduced pressure
  4. additionThe resulting aqueous slurry was diluted with water (50 mL)
  5. extractionwas extracted with dichloromethane (2×50 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0a122de7f1634d819c95b57edaab530c
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897767B2

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