[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]=1A 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.
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