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

HRID 2104596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2104596
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fdb8d05f91564052b6024c70a47bd1a3
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576215B2

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