Triethylamine → 8-benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinoline

HRID 598381Notes

Reaction equation

HRID 598381 reaction equation
C(N(CC)CC)C.Cl.[CH2:9]([O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][C:21]([NH:27][C:28](=O)[CH2:29][O:30][CH2:31][CH3:32])=[C:20]2[NH:34][CH2:35][CH2:36][CH3:37])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][C:24]2[N:23]=[CH:22][C:21]3[N:27]=[C:28]([CH2:29][O:30][CH2:31][CH3:32])[N:34]([CH2:35][CH2:36][CH3:37])[C:20]=3[C:19]=2[CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 67051145N-(6-benzyloxy-4-propylaminoquinolin-3-yl)-2-ethoxyacetamide hydrochloride

Product 1

HCID 670511278-benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolineYield 100.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (32.9 mL, 0.24 mol) was added to a solution of N-(6-benzyloxy-4-propylaminoquinolin-3-yl)-2-ethoxyacetamide hydrochloride (25.4 g) in ethanol (250 mL), and the reaction mixture was heated at reflux for 3 hours. The reaction mixture was allowed to cool to ambient temperature. The ethanol was removed under reduced pressure and the residue was dissolved in chloroform. The solution was washed sequentially with water and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure. The resulting oil was dissolved in acetonitrile and concentrated under reduced pressure to yield 22.3 g of 8-benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinoline as a brown, crystalline solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe ethanol was removed under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform
  5. washThe solution was washed sequentially with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationand concentrated under reduced pressure
  9. dissolutionThe resulting oil was dissolved in acetonitrile
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b205d135ec344d2dad3166fc8e44f90b
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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