O-Methylhydroxylamine hydrochloride → HCID 67506074, compound

HRID 2105484Notes

Reaction equation

HRID 2105484 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[N:12]=[CH:13][N:14](C)C.Cl.[CH3:18][O:19]N>C(O)C>[CH3:18][O:19][N:14]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]=[CH:13]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochloride2×HCID 67506192HCID 67506192, compound

Product 1

HCID 67506074HCID 67506074, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N′-(4-chloroquinolin-3-yl)-N,N-dimethylimidoformamide (10.9 g, 46.6 mmol) and O-methylhydroxylamine hydrochloride (3.9 g, 47 mmol) in ethanol (100 mL) was heated at reflux for 4.5 hours. An analysis by LC/MS indicated the reaction was incomplete, and additional O-methylhydroxylamine hydrochloride (2.0 g, 24 mmol) was added. The reaction was heated at reflux overnight, allowed to cool to room temperature, and concentrated under reduced pressure. The work-up and purification procedures described in Part C of Example 19 were followed with the modification that chromatographic purification was carried out eluting with 5% methanol in dichloromethane containing 3 mL of aqueous ammonium hydroxide per liter of eluent. 1-Methoxy-1H-imidazo[4,5-c]quinoline (approximately 3.7 g) was obtained as a red solid.

Workup

  1. temperatureat reflux for 4.5 hours
  2. temperatureThe reaction was heated
  3. temperatureat reflux overnight
  4. concentrationconcentrated under reduced pressure
  5. customThe work-up and purification procedures
  6. customwere followed with the modification that chromatographic purification
  7. washwas carried out eluting with 5% methanol in dichloromethane containing 3 mL of aqueous ammonium hydroxide per liter of eluent

Sources & evidence

ORD record
ord-8fe4e9ac59964b67850dcd92d6a90d92
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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