Potassium Hydroxide → 6-Bromo-2-(3,5-dimethylphenyl)quinoline

HRID 452351

Reaktionsgleichung

Reaktionsgleichung von HRID 452351
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH2:9]O.[CH3:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:20])=O)[CH:15]=[C:14]([CH3:21])[CH:13]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:18]([C:16]1[CH:17]=[C:12]([CH3:11])[CH:13]=[C:14]([CH3:21])[CH:15]=1)[CH:20]=[CH:9]2

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 149211-(3,5-Dimethylphenyl)ethan-1-oneHCID 110308742-Amino-5-bromobenzenemethanol

Produkt 1

HCID 681936816-Bromo-2-(3,5-dimethylphenyl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

(2-Amino-5-bromophenyl)methanol (22 g, 109 mmol), 3,5-dimethylacetophenone (24.2 g, 163 mmol), RuCl2(PPh3)3 (1.05 g, 1.09 mmol), KOH (11.0 g, 196 mmol) were refluxed in 270 mL of toluene for 18 h. Water was collected from the reaction using a Dean-stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with 5% ethyl acetate in hexanes. The product was further purified by Kugelrohr distillation and crystallization from methanol.

Aufarbeitung

  1. customWater was collected from the reaction
  2. filtrationfiltered through a silica gel plug
  3. washeluted with 5% ethyl acetate in hexanes
  4. distillationThe product was further purified by Kugelrohr distillation and crystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-a9c36c0959304e91a3bb17824f1f1a89
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492006B2

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