4-Phenyl-3-(1-Phenylvinyl)-8-(Trifluoromethyl)Quinoline → 4-Phenyl-3-(1-phenylethyl)-8-(trifluoromethyl)quinoline

HRID 2104597Notes

Reaction equation

HRID 2104597 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH2:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>CCO.[Pd]>[C:1]1([C:7]2[C:16]3[C:11](=[C:12]([C:17]([F:20])([F:18])[F:19])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 669135304-Phenyl-3-(1-Phenylvinyl)-8-(Trifluoromethyl)QuinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 669137474-Phenyl-3-(1-phenylethyl)-8-(trifluoromethyl)quinolineYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-phenyl-3-(1-phenylvinyl)-8-(trifluoromethyl)quinoline (0.050 g, 0.133 mmol) and 5% Pd/C (0.010 g) in EtOH (7 mL) is hydrogenated on a Parr shaker (40 psi hydrogen) overnight. The reaction is filtered through Celite and concentrated. The product is chromatographed eluting with 2:98 ethyl acetate:hexanes to afford the title compound (0.051 g). MS (ESI) m/z 378; HRMS: calcd for C24H18F3N+H, 378.14696; found (ESI, [M+H]+), 378.1459.

Workup

  1. filtrationThe reaction is filtered through Celite
  2. concentrationconcentrated
  3. customThe product is chromatographed
  4. washeluting with 2:98 ethyl acetate

Sources & evidence

ORD record
ord-9f7ae130ca0346f086cc829e9eeddd78
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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