5-Bromonicotinamide → 5-Bromonicotinonitrile

HRID 1642169Notes

Reaction equation

HRID 1642169 reaction equation
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

Participants

3

Reactant 2

HCID 18085-BromonicotinamideHCID 24813Phosphorus oxychloride

Product 1

HCID 7367935-BromonicotinonitrileYield 82%

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-9882def7b3524da7a9899f8dfeb4d6b2
Source dataset
uspto-grants-2012_02
Patent number
US08119635B2

Reaction notes

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