Реакция #9561

Уравнение реакции

Butyryl chloride

7-bromo-N4-(2-methylpropyl)quinoline-3,4-diamine

→

7-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinoline

Растворители

pyridine

Условия реакции

Обработка

1. 1
   ДругоеA pale yellow precipitate formed
2. 2
   ТемператураThe reaction mixture was heated
3. 3
   Температураat reflux for eight hours
4. 4
   Концентрированиеwas concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in 1 N hydrochloric acid
6. 6
   workup.ADDITIONadjusted to pH 14 with the addition of 10% aqueous sodium hydroxide
7. 7
   ДругоеA precipitate formed
8. 8
   Другоеwas isolated by filtration
9. 9
   Промывкаwashed with water (3×100 mL)
10. 10
    Другоеdried overnight on the filter funnel

Методика

Butyryl chloride (1.1 equivalent) was slowly added to a stirred solution of 7-bromo-N4-(2-methylpropyl)quinoline-3,4-diamine (52.9 g, 0.18 mol.) in pyridine (700 mL) at room temperature. A pale yellow precipitate formed and then went into solution. The reaction mixture was heated at reflux for eight hours, and then allowed to slowly cool to room temperature over the weekend. The dark gold, turbid reaction mixture was concentrated under reduced pressure. The residue was dissolved in 1 N hydrochloric acid and then adjusted to pH 14 with the addition of 10% aqueous sodium hydroxide. A precipitate formed, was isolated by filtration, washed with water (3×100 mL), and dried overnight on the filter funnel to provide 7-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinoline as an off-white solid.

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