Reaktion #9569

Reaktionsgleichung

2,5-Dimethoxytetrahydrofuran

8-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

→

1-(2-methylpropyl)-8-(1-pyrrolyl)-1H-imidazo[4,5-c]quinolin-4-amine

Ausbeute 57.3%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was heated
2. 2
   Temperaturat reflux for one hour
3. 3
   EinengenThe resulting dark brown solution was concentrated under reduced pressure
4. 4
   workup.ADDITIONthe residue was mixed with water
5. 5
   workup.ADDITIONThe resulting mixture was made basic with the addition of ammonium hydroxide
6. 6
   SonstigeThe resulting precipitate was isolated by filtration
7. 7
   Waschenwashed with water
8. 8
   Sonstigedried
9. 9
   Sonstigerecrystallized from ethanol (100 mL)
10. 10
    SonstigeThe crystals were collected in three crops
11. 11
    SonstigeThe first crop was dried for a day in a vacuum oven at 100° C.

Vorschrift

2,5-Dimethoxytetrahydrofuran (1.6 mL of 95%, 12 mmol) was added to a suspension of 8-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (3.0 g, 12 mmol) in acetic acid (60 mL), and the reaction was heated at reflux for one hour. The resulting dark brown solution was concentrated under reduced pressure, and the residue was mixed with water. The resulting mixture was made basic with the addition of ammonium hydroxide and stirred for 30 minutes. The resulting precipitate was isolated by filtration, washed with water, dried, and recrystallized from ethanol (100 mL). The crystals were collected in three crops. The first crop was dried for a day in a vacuum oven at 100° C. to provide 2.1 g of 1-(2-methylpropyl)-8-(1-pyrrolyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid, mp 227.5–231.5° C.

Quelle