Реакция #9569

Уравнение реакции

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

Выход 57.3%

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   Температураthe reaction was heated
2. 2
   Температураat reflux for one hour
3. 3
   КонцентрированиеThe 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
   ДругоеThe resulting precipitate was isolated by filtration
7. 7
   Промывкаwashed with water
8. 8
   Другоеdried
9. 9
   Другоеrecrystallized from ethanol (100 mL)
10. 10
    ДругоеThe crystals were collected in three crops
11. 11
    ДругоеThe first crop was dried for a day in a vacuum oven at 100° C.

Методика

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.

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