反応 #9595

反応方程式

N-[2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]methanesulfonamide

valeryl chloride

→

N-[2-(7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide

溶媒

pyridine

反応条件

後処理

1. 1
   温度The reaction mixture was then heated
2. 2
   温度at reflux for 12 hours
3. 3
   濃縮concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was mostly dissolved in 10% HCl
5. 5
   workup.ADDITIONThe resulting suspension was adjusted to pH 12 with the addition of 50% aqueous sodium hydroxide
6. 6
   その他A precipitate formed
7. 7
   その他was isolated by filtration
8. 8
   その他air-dried

実験手順

To a stirred solution of N-[2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]methanesulfonamide (46.4 g, 0.129 mol) in 1000 mL pyridine was slowly added valeryl chloride (1.1 equivalents). After 1.5 hours the mixture was yellow and turbid. The reaction mixture was then heated at reflux for 12 hours, allowed to cool to ambient temperature and concentrated under reduced pressure. The residue was mostly dissolved in 10% HCl to adjust to pH 1. The resulting suspension was adjusted to pH 12 with the addition of 50% aqueous sodium hydroxide and stirred overnight. A precipitate formed and was isolated by filtration and air-dried to provide 45 g of N-[2-(7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide as a pale gray/green solid.

出典