O-Methylhydroxylamine hydrochloride → HCID 67505819, compound

HRID 2105488Notes

Reaction equation

HRID 2105488 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[NH:12][C:13](=O)[CH:14]([CH3:16])[CH3:15].Cl.[CH3:19][O:20][NH2:21]>C(O)C>[CH:14]([C:13]1[N:21]([O:20][CH3:19])[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]=1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 67505834N-(4-chloroquinolin-3-yl)-2-methylpropanamide

Product 1

HCID 67505819HCID 67505819, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-chloroquinolin-3-yl)-2-methylpropanamide (6.0 g, 24 mmol), O-methylhydroxylamine hydrochloride (2.5 g, 0.030 mol), and ethanol (75 mL) was heated at reflux for five hours, allowed to cool to room temperature, stirred overnight, and concentrated under reduced pressure. The residue was dissolved in dichloromethane (100 mL), and the solution was washed with saturated aqueous sodium carbonate (2×50 mL) dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 4.9 g of 2-isopropyl-1-methoxy-1H-imidazo[4,5-c]quinoline as a dark oil.

Workup

  1. temperatureat reflux for five hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  4. washthe solution was washed with saturated aqueous sodium carbonate (2×50 mL)
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c64770c734a845a1aa82838330b66966
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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