반응 #9543

반응 방정식

Trimethyl orthobutyrate

pyridine hydrochloride

1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol

→

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

수율 76.7%

용매

toluene

—

Hexanes

반응 조건

후처리

1. 1
   온도the reaction was heated
2. 2
   온도at reflux for two hours
3. 3
   기타The solvent was removed under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane
5. 5
   세척washed with water
6. 6
   기타The dichloromethane was removed under reduced pressure until a precipitate
7. 7
   기타to form
8. 8
   기타the precipitate was isolated by filtration

실험 절차

Trimethyl orthobutyrate (11.61 mL, 72.6 mmol) and catalytic pyridine hydrochloride were added to a solution of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (22.51 g, 72.6 mmol) in anhydrous toluene (120 mL), and the reaction was heated at reflux for two hours. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was removed under reduced pressure until a precipitate began to form. Hexanes were added, and the precipitate was isolated by filtration to provide 20.17 g of 1-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

출처