Quinoline → 2-Chloro-5-(trifluoromethyl)nicotinonitrile

HRID 132841

Reaktionsgleichung

Reaktionsgleichung von HRID 132841
P(Cl)(Cl)([Cl:3])=O.N1C2C(=CC=CC=2)C=CC=1.[C:16]([C:18]1[C:19](O)=[N:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)#[N:17].C(=O)(O)[O-].[Na+]>O>[Cl:3][C:19]1[C:18]([C:16]#[N:17])=[CH:23][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:21][N:20]=1

Komponenten

6

Edukt 4

HCID 7047QuinolineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 148370202-Oxo-5-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 200715992-Chloro-5-(trifluoromethyl)nicotinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of phosphorous oxychloride (13.4 mL, 144 mmol) and quinoline (8.7 mL, 73 mmol) was added the product from Step C above (24.6 g, 131 mmol) and the resultant mixture was heated to reflux for 3 h. The reaction was cooled to 100° C. before water (70 mL) was slowly added. The mixture was further cooled to room temperature and neutralized by the cautious addition of saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with three portions of ethyl acetate and the organic layers were combined, dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to afford the desired compound. 1H NMR (500 MHz, CDCl3) δ 8.88 (d, J=2.0 Hz, 1H), 8.26 (d, J=2.5 Hz, 1H).

Aufarbeitung

  1. temperatureto reflux for 3 h
  2. additionwas slowly added
  3. extractionThe aqueous layer was extracted with three portions of ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-15754b359c6e4374b7dbfa22f34c8819
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388019B2

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