Реакция #9477

Уравнение реакции

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

Выход 49.3%

Растворители

water

ethanol

Условия реакции

Обработка

1. 1
   Температураthe reaction was heated
2. 2
   Температураat reflux under a nitrogen atmosphere for two hours
3. 3
   ТемператураUpon cooling
4. 4
   Другоеthe reaction
5. 5
   Другоеa precipitate formed
6. 6
   Другоеwas isolated by filtration
7. 7
   ДругоеThe solid was purified by flash column chromatography on silica gel (
8. 8
   Промывкаeluting sequentially with chloroform, 99:1 chloroform

Методика

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.

Источник