5-Bromonicotinamide → 5-Bromonicotinonitrile

HRID 393788

Reaktionsgleichung

Reaktionsgleichung von HRID 393788
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([CH:15]=1)[C:12]([NH2:14])=O>>[Br:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:12]#[N:14])[CH:15]=1

Komponenten

3

Edukt 2

HCID 18085-BromonicotinamideHCID 24813Phosphorus oxychloride

Produkt 1

HCID 7367935-BromonicotinonitrileAusbeute 82 %

Versuchsvorschrift

Phosphorus oxychloride (5 ml) was added to 5-bromonicotinamide (2 g, 10 mmol, Avocado Research Chemicals, Ltd.) and the mixture was heated to gentle reflux for 3 hours. The mixture was allowed to cool to room temperature, poured onto ice (100 g) and extracted with ethyl acetate (3×100 mL). The combined extracts were washed successively with aqueous ammonium hydroxide and water, dried (MgSO4), filtered and the filtrate concentrated under reduced pressure. The residue was purified by chromatography (SiO2, ethyl acetate:hexanes, 1:1) to provide the title compound (1.5 g, 82% yield). MS (DCI/NH3) m/z 184 (M+H)+.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto gentle reflux for 3 hours
  3. additionpoured onto ice (100 g)
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe combined extracts were washed successively with aqueous ammonium hydroxide and water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customThe residue was purified by chromatography (SiO2, ethyl acetate:hexanes, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-5ed26cd2492b48b394801e0e509cf8f4
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809105B2

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