Reaction #9571

Reaction equation

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

triethyl orthoformate

pyridine hydrochloride

→

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

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux overnight
3. 3
   ConcentrationThe reaction mixture was concentrated under reduced pressure
4. 4
   Otherthe residue was purified by HPFC (
5. 5
   Washeluting with chloroform

Procedure

A mixture of 5-bromo-N4-(2-methylpropyl)quinoline-3,4-diamine (1.0 g, 3.4 mmol), triethyl orthoformate (0.9 mL, 5 mmol), and pyridine hydrochloride (117 mg, 1.0 mmol) in acetonitrile (17 mL) was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 70:30) to provide 9-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline as a dark oil.

Source