Hydrochloric Acid → 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butylamine

HRID 1818138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818138
Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[C:14]([CH2:28][O:29][CH2:30][CH3:31])=[N:13][C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1>C(O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[C:14]([CH2:28][O:29][CH2:30][CH3:31])=[N:13][C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86593758tert-butyl[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate

Produkt 1

HCID 219843404-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butylamineAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Concentrated hydrochloric acid (15.6 mL, 0.194 mol) was added to a solution of tert-butyl [4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate (23.2 g, 48 mmol) in ethanol, and the reaction was heated at reflux for 20 minutes. A precipitate formed, and the reaction was allowed to cool to ambient temperature overnight. The solid was isolated by filtration, washed with ethanol, and dissolved in water. The solution was washed with dichloromethane and then made basic with the addition of 50% aqueous sodium hydroxide. The basic solution was extracted with dichloromethane (3×300 mL), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 17 g of 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butylamine as an off-white solid.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 20 minutes
  3. customA precipitate formed
  4. customThe solid was isolated by filtration
  5. washwashed with ethanol
  6. dissolutiondissolved in water
  7. washThe solution was washed with dichloromethane
  8. additionmade basic with the addition of 50% aqueous sodium hydroxide
  9. extractionThe basic solution was extracted with dichloromethane (3×300 mL)
  10. dry with materialthe combined extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5559e3ad660d4b4bbc0fcbc05636bf79
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598382B2

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