O-ethylhydroxylamine hydrochloride → 1-ethoxy-1H-imidazo[4,5-c]quinoline

HRID 2105480Notes

Reaction equation

HRID 2105480 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][CH:13]=O.Cl.[CH2:16]([O:18][NH2:19])[CH3:17]>C(O)(C)C>[CH2:16]([O:18][N:19]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)[CH3:17]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 86227468N-(4-chloroquinolin-3-yl)formamide

Product 1

HCID 675069551-ethoxy-1H-imidazo[4,5-c]quinolineYield 47.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-chloroquinolin-3-ylformamide (5.0 g, 24 mmol), O-ethylhydroxylamine hydrochloride (2.95 g, 30.2 mmol), and isopropanol (75 mL) was heated at reflux overnight, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was stirred with dichloromethane (150 mL) and saturated aqueous sodium carbonate (50 mL) for 15 minutes. The organic layer was separated and dried over potassium carbonate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 2% methanol in dichloromethane containing 5 mL of aqueous ammonium hydroxide per liter of eluent) to provide 2.45 g of 1-ethoxy-1H-imidazo[4,5-c]quinoline.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated under reduced pressure
  3. customThe organic layer was separated
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (eluting with 2% methanol in dichloromethane containing 5 mL of aqueous ammonium hydroxide per liter of eluent)

Sources & evidence

ORD record
ord-a91af1a69f174bea8db4f7f02889b41c
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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