Potassium Hydroxide → 2-(3,5-Dimethylphenyl)-5-(trifluoromethyl)quinoline

HRID 1056442Notes

Reaction equation

HRID 1056442 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH2:12]O.[CH3:14][C:15]1[CH:16]=[C:17]([C:22](=O)[CH3:23])[CH:18]=[C:19]([CH3:21])[CH:20]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[CH3:14][C:15]1[CH:16]=[C:17]([C:22]2[CH:23]=[CH:12][C:3]3[C:2](=[CH:7][CH:6]=[CH:5][C:4]=3[C:8]([F:11])([F:10])[F:9])[N:1]=2)[CH:18]=[C:19]([CH3:21])[CH:20]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 149211-(3,5-Dimethylphenyl)ethan-1-oneHCID 54486842HCID 54486842, compound

Product 1

HCID 1212668222-(3,5-Dimethylphenyl)-5-(trifluoromethyl)quinolineYield 35.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (2-amino-6-(trifluoromethyl)phenyl)methanol (18 g, 94 mmol), 1-(3,5-dimethylphenyl)ethanone (19.5 ml, 130 mmol), powdered potassium hydroxide (0.90 g, 16.0 mmol), and RuCl2(PPh3)3 (0.45 g, 0.47 mmol) in toluene (310 ml) was refluxed overnight. Upon cooling to room temperature, the mixture was washed with water and extracted with ethyl acetate (3 times). The crude material was coated on celite and purified by CC starting with 5% EA in Heptanes. The product Obtained was recrystallized from methanol to afford 2-(3,5-dimethylphenyl)-5-(trifluoromethyl)quinoline (10 g, 35% yield) as yellow crystals.

Workup

  1. temperaturewas refluxed overnight
  2. washthe mixture was washed with water
  3. extractionextracted with ethyl acetate (3 times)
  4. custompurified by CC
  5. customThe product Obtained
  6. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-72f09dc8148e45afacc8d6bc22c4a6e0
Source dataset
uspto-grants-2016_07
Patent number
US09397302B2

Reaction notes

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