Sodium Hydroxide → 1-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 9381

Reaktionsgleichung

Reaktionsgleichung von HRID 9381
[OH-].[Na+].[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])=[C:9]([NH:14][C:15](=O)[CH2:16][O:17][CH2:18][CH3:19])[CH:10]=[N:11]2)=[CH:6][CH:5]=1>O.C(O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:21]([CH2:22][C:23]([CH3:25])([OH:26])[CH3:24])[C:15]([CH2:16][O:17][CH2:18][CH3:19])=[N:14][C:9]=3[CH:10]=[N:11][C:12]=2[CH:13]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 21984424N-[7-bromo-4-(2-hydroxy-2-methylpropylamino)quinolin-3-yl]-2-ethoxyacetamide

Produkt 1

HCID 219840281-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-olAusbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of sodium hydroxide (25 g, 0.625 mol) in water (205 mL) was added to a solution of N-[7-bromo-4-(2-hydroxy-2-methylpropylamino)quinolin-3-yl]-2-ethoxyacetamide (170.88 g, 0.431 mol) in ethanol (700 mL), and the reaction was heated at reflux under a nitrogen atmosphere for two hours. Upon cooling the reaction, a precipitate formed and was isolated by filtration. The solid was purified by flash column chromatography on silica gel (eluting sequentially with chloroform, 99:1 chloroform:methanol, and 97:3 chloroform:methanol) to provide 80.31 g of 1-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a tan solid.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureat reflux under a nitrogen atmosphere for two hours
  3. temperatureUpon cooling
  4. customthe reaction
  5. customa precipitate formed
  6. customwas isolated by filtration
  7. customThe solid was purified by flash column chromatography on silica gel (
  8. washeluting sequentially with chloroform, 99:1 chloroform

Quellen und Nachweise

ORD-Eintrag
ord-2ad48777879c49898552a1d3c495787b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

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