O-ethylhydroxylamine hydrochloride → 1-ethoxy-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 2105463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105463
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].Cl[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[NH:17][C:18](=O)[CH2:19][CH2:20][CH3:21]>C(O)C>[CH2:2]([O:4][N:5]1[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=[C:18]1[CH2:19][CH2:20][CH3:21])[CH3:3]

Komponenten

4

Edukt 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 57447109HCID 57447109, Verbindung

Produkt 1

HCID 675069631-ethoxy-2-propyl-1H-imidazo[4,5-c]quinolineAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethoxyamine hydrochloride (2.34 g, 2.0 eq) was added to a solution of N-(4-chloroquinolin-3-yl)butyramide (3.0 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 2.89 g of 1-ethoxy-2-propyl-1H-imidazo[4,5-c]quinoline.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e7ded51ddc1846c2b28dda462bddf8a4
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579359B2

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