Ethoxyacetyl chloride → HCID 67051012, Verbindung

HRID 2383140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383140
[CH2:1]([O:3][CH2:4][C:5](Cl)=O)[CH3:2].[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[CH:21][C:20]([NH2:26])=[C:19]2[NH:27][CH2:28][CH:29]([CH3:31])[CH3:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[CH2:8]([O:15][C:16]1[CH:25]=[CH:24][C:23]2[N:22]=[CH:21][C:20]3[N:26]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:27]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:19]=3[C:18]=2[CH:17]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 84189Ethoxyacetyl chlorideHCID 67050972HCID 67050972, Verbindung

Produkt 1

HCID 67051012HCID 67051012, VerbindungAusbeute 32,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Ethoxyacetyl chloride (3.81 g, 31.1 mmol) was slowly added to a chilled solution of 6-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine (9.1 g, 28.3 mmol) in pyridine (60 mL). The reaction was allowed to warm to ambient temperature and then heated at reflux for three hours. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane (200 mL). The resulting solution was washed with water (3×100 mL) and concentrated under reduced pressure. The concentrated solution was passed through a layer of silica gel (eluting with dichloromethane:methanol 95:5) and concentrated under reduced pressure to provide 3.6 g of 8-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline as an oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for three hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane (200 mL)
  5. washThe resulting solution was washed with water (3×100 mL)
  6. concentrationconcentrated under reduced pressure
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-28f70738242342b9b28e3f7f55e3facd
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263594B2

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