Dimethylformamide → 2-Chloro-4-(trifluoromethyl)quinoline

HRID 513732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513732
CN(C=O)C.[F:6][C:7]([F:20])([F:19])[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10](=O)[CH:9]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:10]1[CH:9]=[C:8]([C:7]([F:20])([F:19])[F:6])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 27593472-Hydroxy-4-(trifluoromethyl)quinoline

Produkt 1

HCID 27829122-Chloro-4-(trifluoromethyl)quinolineAusbeute 29 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

DMF (cat.) was added to a solution of 4-trifluoromethyl-1H-quinolin-2-one 465 (160 mg, 0.75 mmol) in POCl3 (2 ml) and the mixture was heated at 90° C. for 1 h. After cooling, the mixture was concentrated in vacuo and the residue was poured into an ice cold solution of NaHCO3 solution. The aqueous phase was extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the title compound (50 mg, 29%) which was used in the next step without further purification.

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. additionthe residue was poured into an ice cold solution of NaHCO3 solution
  4. extractionThe aqueous phase was extracted with EtOAc
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-79f1f1d9d02242dda64edece07364eac
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102688B2

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