Sodium Hydroxide → HCID 22254517, Verbindung

HRID 434005

Reaktionsgleichung

Reaktionsgleichung von HRID 434005
[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[C:20]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:21]=1[CH3:28].[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][CH2:28][C:21]2[CH:20]=[CH:25][C:24]([C:26]#[N:27])=[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 140048403-Bromo-4-methylbenzonitrileHCID 21898023HCID 21898023, Verbindung

Produkt 1

HCID 22254517HCID 22254517, VerbindungAusbeute 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 cc-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, Rf0.48) 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, Rf0.48)

Quellen und Nachweise

ORD-Eintrag
ord-e012e80795af4fd1b38d7c43054bad18
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670372B2

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