O-ethylhydroxylamine hydrochloride → 1-ethoxy-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 2105463Notes

Reaction equation

HRID 2105463 reaction equation
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].Cl[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[NH:17][C:18](=O)[CH2:19][CH2:20][CH3:21]>C(O)C>[CH2:2]([O:4][N:5]1[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=[C:18]1[CH2:19][CH2:20][CH3:21])[CH3:3]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 57447109HCID 57447109, compound

Product 1

HCID 675069631-ethoxy-2-propyl-1H-imidazo[4,5-c]quinolineYield 93.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethoxyamine hydrochloride (2.34 g, 2.0 eq) was added to a solution of N-(4-chloroquinolin-3-yl)butyramide (3.0 g, 1.0 eq) in ethanol (75 mL). The reaction mixture was heated at reflux for 3 hours, cooled to ambient temperature, and then concentrated under reduced pressure. The residue was partitioned between dichloromethane and aqueous saturated sodium bicarbonate. The organic layer was separated and concentrated under reduced pressure to provide 2.89 g of 1-ethoxy-2-propyl-1H-imidazo[4,5-c]quinoline.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between dichloromethane and aqueous saturated sodium bicarbonate
  5. customThe organic layer was separated
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7ded51ddc1846c2b28dda462bddf8a4
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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