Benzyloxyamine hydrochloride → 1-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 2105460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105460
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][CH2:15][CH3:16].Cl.[CH2:19]([O:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([O:26][N:27]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]=[C:13]1[CH2:14][CH2:15][CH3:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 102312Benzyloxyamine hydrochlorideHCID 57447109HCID 57447109, Verbindung

Produkt 1

HCID 675064061-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinolineAusbeute 29,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of N-(4-chloroquinolin-3-yl)butyramide (3.3 g, 13 mmol, 1.0 eq) and O-benzylhydroxylamine hydrochloride (4.23 g, 26.5 mmol, 2.0 eq) in ethanol (150 mL) was heated at reflux for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 3% methanol in dichloromethane) to provide 1.20 g of 1-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline.

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel eluting with 3% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-4764ffd81499413cb32566c89cd248a3
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579359B2

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