Sodium Hydroxide → 4-{[2-(1H-imidazo[4,5-c]quinolin-1-yl)butoxy]methyl}benzonitrile

HRID 1839125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1839125
[N:1]1([CH:14]([CH2:17][CH3:18])[CH2:15][OH:16])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[N:1]1([CH:14]([CH2:17][CH3:18])[CH2:15][O:16][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 869964-(Bromomethyl)benzonitrileHCID 218980232-(1H-imidazo[4,5-c]quinolin-1-yl)-1-butanol

Produkt 1

HCID 222545174-{[2-(1H-imidazo[4,5-c]quinolin-1-yl)butoxy]methyl}benzonitrileAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-(1H-imidazo[4,5-c]quinolin-1-yl)-1-butanol (3.0 g, 12.4 mmol) was added to a stirring mixture of α-bromo-p-tolunitrile (3.0 g, 15.3 mmol), sodium hydroxide (40 ml, 50%), dichloromethane (40 ml), and benzyltrimethylammonium chloride (0.02 g, 0.11 mmol). The reaction was maintained for 72 hours and then diluted with dichloromethane (100 ml) and water (100 ml). The phases were separated and the aqueous phase was extracted with additional dichloromethane (100 ml). The organic fractions were combined, washed with water, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 9/1 dichloromethane/methanol, Rf 0.48) to provide 2.66 g of 4-{[2-(1H-imidazo[4,5-c]quinolin-1-yl)butoxy]methyl}benzonitrile.

Aufarbeitung

  1. temperatureThe reaction was maintained for 72 hours
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with additional dichloromethane (100 ml)
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (silica gel, 9/1 dichloromethane/methanol, Rf 0.48)

Quellen und Nachweise

ORD-Eintrag
ord-bc654a5c58914cc48692338e40308d24
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677348B2

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