O-(propan-2-yl)hydroxylamine hydrochloride → HCID 67506063, compound

HRID 2105466Notes

Reaction equation

HRID 2105466 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)[CH2:20][CH3:21]>C(O)C>[CH2:20]([C:19]1[N:6]([O:5][CH:2]([CH3:4])[CH3:3])[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]=1)[CH3:21]

Participants

4

Reactant 2

HCID 12696235O-(propan-2-yl)hydroxylamine hydrochlorideHCID 57853761HCID 57853761, compound

Product 1

HCID 67506063HCID 67506063, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

O-isopropylhydroxylamine hydrochloride (2.5 g, 1.7 eq) was added to a solution of N-(4-chloroquinolin-3-yl)propionamide (3.1 g, 1.0 eq) in ethanol (150 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 3.2 g of 2-ethyl-1-isopropoxy-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-c6b7ef2ed7d743bbb4a8d073a6151c56
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

Loading…