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

HRID 9475Notes

Reaction equation

HRID 9475 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[C:5]([NH2:12])[CH:6]=[N:7]2.[CH:18](OCC)(OCC)OCC.Cl.N1C=CC=CC=1>C(#N)C>[Br:1][C:2]1[C:3]2[C:4]3[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH:18]=[N:12][C:5]=3[CH:6]=[N:7][C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 10176127Pyridinium chlorideHCID 68819348HCID 68819348, compound

Product 1

HCID 219843489-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by HPFC (
  5. washeluting with chloroform

Sources & evidence

ORD record
ord-85819ad6c6834adb8e5accf545355994
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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