Reacción #9569

Ecuación de reacción

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

Rendimiento 57.3%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction was heated
2. 2
   Temperaturaat reflux for one hour
3. 3
   ConcentraciónThe 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
   OtroThe resulting precipitate was isolated by filtration
7. 7
   Lavadowashed with water
8. 8
   Otrodried
9. 9
   Otrorecrystallized from ethanol (100 mL)
10. 10
    OtroThe crystals were collected in three crops
11. 11
    OtroThe first crop was dried for a day in a vacuum oven at 100° C.

Procedimiento

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.

Fuente