Dimethylformamide → 5-Nitropicolinonitrile

HRID 1858013Notes

Reaction equation

HRID 1858013 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][N:12](C=O)C>C(Cl)Cl>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:11]#[N:12])=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 782402-Bromo-5-nitropyridine

Product 1

HCID 102612365-Nitropicolinonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising 2-bromo-5-nitropyridine (5.6 g, 27.7 mmol), cuprous cyanide (2.5 g, 27.4 mmol) and DMF (5 mL) was heated at 105° C. for 2.5 hours, cooled and diluted with methylene chloride (200 mL). The mixture was stirred 20 minutes, filtered and concentrated under reduced pressure. The residue was dissolved in methylene chloride and the solution was washed sequentially with 2N sodium hydroxide (150 mL), 7M ammonium hydroxide (150 mL) and water (150 mL), dried (MgSO4), filtered and concentrated under reduced pressure to provide 5-nitropyridine-2-carbonitrile (3.14 g, 21 mmol) as a yellow oil. 1H-NMR (300 Mhz, DMSO-d6): 8.4 (d, 1H), 8.8 (d, 1H), 9.5 (s, 1H); MS (EI); Calculated for C6H3N3O2, 149.1, Found (MH+): 149.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washthe solution was washed sequentially with 2N sodium hydroxide (150 mL), 7M ammonium hydroxide (150 mL) and water (150 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f96668eefc664e46a89ba7f7b4af183d
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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