Hydrochloric Acid → 4-Phenyl-3-(1-Phenylvinyl)-8-(Trifluoromethyl)Quinoline

HRID 2104596Notes

Reaction equation

HRID 2104596 reaction equation
[C:1]1([C:7]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[C:26]([F:29])([F:28])[F:27])(O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O>CCO>[C:20]1([C:19]2[C:18]3[C:13](=[C:14]([C:26]([F:29])([F:27])[F:28])[CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11][C:10]=2[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH2:8])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 113498961-Phenyl-1-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]ethanol

Product 1

HCID 669135304-Phenyl-3-(1-Phenylvinyl)-8-(Trifluoromethyl)QuinolineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-phenyl-1-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]ethanol (0.675 g, 1.72 mmol) in EtOH (13 mL) is refluxed with conc HCl (2.6 mL) for 2 h. The cooled reaction is poured into water and extracted with methylene chloride. The extract is washed with saturated aq sodium bicarbonate, dried (MgSO4) and concentrated. The residue is chromatographed eluting with 5:95 ethyl acetate:hexane to afford the title compound as a yellow solid (0.546 g, 85%). MS (ESI) m/z 376; HRMS: calcd for C24H16F3N+H, 376.13131; found (ESI, [M+H]+), 376.1306.

Workup

  1. customThe cooled reaction
  2. extractionextracted with methylene chloride
  3. washThe extract is washed with saturated aq sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is chromatographed
  7. washeluting with 5:95 ethyl acetate

Sources & evidence

ORD record
ord-fdb8d05f91564052b6024c70a47bd1a3
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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