O-(propan-2-yl)hydroxylamine hydrochloride → HCID 67506144, compound

HRID 2105478Notes

Reaction equation

HRID 2105478 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)[CH2:14][O:15][CH2:16][CH3:17].Cl.[CH:20]([O:23][NH2:24])([CH3:22])[CH3:21]>C(O)C>[CH2:16]([O:15][CH2:14][C:13]1[N:24]([O:23][CH:20]([CH3:22])[CH3:21])[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)[CH3:17]

Participants

4

Reactant 2

HCID 12696235O-(propan-2-yl)hydroxylamine hydrochlorideHCID 57429982HCID 57429982, compound

Product 1

HCID 67506144HCID 67506144, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-chloroquinolin-3-yl)-2-ethoxyacetamide (7.3 g, 28 mmol) and O-isopropylhydroxylamine hydrochloride (3.3 g, 0.030 mol) in ethanol (150 mL) was heated at reflux for two hours, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 4% methanol in dichloromethane containing 3 mL of aqueous ammonium hydroxide per liter of eluent) to provide 2.15 g of 2-(ethoxymethyl)-1-isopropoxy-1H-imidazo[4,5-c]quinoline as a dark oil that crystallized upon standing.

Workup

  1. temperatureat reflux for two hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluting with 4% methanol in dichloromethane containing 3 mL of aqueous ammonium hydroxide per liter of eluent)

Sources & evidence

ORD record
ord-7ded96022aa2477d9ec47629698997e9
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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