Benzyloxyamine hydrochloride → 1-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 2105499Notes

Reaction equation

HRID 2105499 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[CH2:14][CH2:15][CH3:16].Cl.[CH2:19]([O:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([O:26][N:27]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=[C:13]1[CH2:14][CH2:15][CH3:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:14]([C:13]1[N:27]([OH:26])[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=1)[CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 57447109HCID 57447109, compound

Product 2

HCID 675064061-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinolineHCID 675069482-propyl-1H-imidazo[4,5-c]quinolin-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-chloroquinolin-3-yl)butyramide (20.0 g, 80.4 mmol) and O-benzylhydroxylamine hydrochloride (16.0 g, 0.100 mol) in ethanol (150 mL) was heated at reflux overnight and allowed to cool to room temperature. A precipitate was present, and the mixture was cooled to approximately 0° C. The precipitate was collected by filtration and purified by column chromatography on silica gel (eluting with 5% methanol in dichloromethane containing 3 mL of aqueous ammonium hydroxide per liter of eluent) to provide 1-(benzyloxy)-2-propyl-1H-imidazo[4,5-c]quinoline and 2-propyl-1H-imidazo[4,5-c]quinolin-1-ol.

Workup

  1. temperatureat reflux overnight
  2. temperaturethe mixture was cooled to approximately 0° C
  3. filtrationThe precipitate was collected by filtration
  4. custompurified by column chromatography on silica gel (eluting with 5% methanol in dichloromethane containing 3 mL of aqueous ammonium hydroxide per liter of eluent)

Sources & evidence

ORD record
ord-598bdfcb84b4441e870518b70bef15d2
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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