O-Methylhydroxylamine hydrochloride → HCID 67506760, compound

HRID 2105465Notes

Reaction equation

HRID 2105465 reaction equation
Cl.[CH3:2][O:3][NH2:4].Cl[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][C:7]=1[NH:16][C:17](=O)[CH2:18][CH3:19]>C(O)C>[CH2:18]([C:17]1[N:4]([O:3][CH3:2])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH3:19]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 57853761HCID 57853761, compound

Product 1

HCID 67506760HCID 67506760, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

O-methylhydroxylamine hydrochloride (1.51 g, 1.7 eq) was added to a solution of N-(4-chloroquinolin-3-yl)propionamide (2.5 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 2.10 g of 2-ethyl-1-methoxy-1H-imidazo[4,5-c]quinoline as a brown solid.

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-a1e8f7ad1d4a4dee853d0b9838e6686f
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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