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

HRID 452351

Reaction equation

HRID 452351 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-a9c36c0959304e91a3bb17824f1f1a89
Source dataset
uspto-grants-2013_07
Patent number
US08492006B2

Linked notes

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