Reaktion #9477

Reaktionsgleichung

sodium hydroxide

N-[7-bromo-4-(2-hydroxy-2-methylpropylamino)quinolin-3-yl]-2-ethoxyacetamide

→

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

Ausbeute 49.3%

Lösungsmittel

water

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was heated
2. 2
   Temperaturat reflux under a nitrogen atmosphere for two hours
3. 3
   TemperaturUpon cooling
4. 4
   Sonstigethe reaction
5. 5
   Sonstigea precipitate formed
6. 6
   Sonstigewas isolated by filtration
7. 7
   SonstigeThe solid was purified by flash column chromatography on silica gel (
8. 8
   Wascheneluting sequentially with chloroform, 99:1 chloroform

Vorschrift

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.

Quelle