Phosphorus oxychloride → Ethyl 4-chloro-7-(trifluoromethyl)quinoline-3-carboxylate

HRID 1662155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662155
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178469560HCID 178469560, Verbindung

Produkt 1

HCID 14515676Ethyl 4-chloro-7-(trifluoromethyl)quinoline-3-carboxylate

Versuchsvorschrift

Ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate (Aldrich, 10.0 g, 35.1 mmol) and phosphorus oxychloride (100 mL, 1.07 mol) were refluxed for 2 hours. After cooling the mixture was poured onto ice (1.0 L) and stirred for 1 hour. The mixture was extracted twice with dichloromethane (500 mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.40 (t, J=7.12 Hz, 3H), 4.46 (q, J=7.12 Hz, 2H), 8.14 (d, J=8.82 Hz, 1H), 8.54 (s, 1H), 8.62 (d, J=8.82 Hz, 1H), 9.30 (s, 1H). MS (ESI) m/z 303.95 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. additionwas poured onto ice (1.0 L)
  3. extractionThe mixture was extracted twice with dichloromethane (500 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-aeebefbea69d4f3ea9a7665a89bdcfda
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030504B2

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