O-(propan-2-yl)hydroxylamine hydrochloride → 1-isopropoxy-2-methyl-1H-imidazo[4,5-c]quinoline

HRID 2105468Notes

Reaction equation

HRID 2105468 reaction equation
Cl.[CH:2]([O:5][NH2:6])([CH3:4])[CH3:3].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[NH:18][C:19](=O)[CH3:20]>C(O)C>[CH:2]([O:5][N:6]1[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=[C:19]1[CH3:20])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 12696235O-(propan-2-yl)hydroxylamine hydrochlorideHCID 67506066HCID 67506066, compound

Product 1

HCID 675069571-isopropoxy-2-methyl-1H-imidazo[4,5-c]quinolineYield 94.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

O-isopropylhydroxylamine hydrochloride (2.14 g, 1.7 eq) was added to a solution of N-(4-chloroquinolin-3-yl)acetamide (2.51 g, 1.0 eq) in ethanol (75 mL). The reaction mixture was heated at reflux for 2 hours 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 2.60 g of 1-isopropoxy-2-methyl-1H-imidazo[4,5-c]quinoline.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 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-99402be581c2418b986372e7204598b8
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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