Ammonia → 5-Cyanonicotinamide

HRID 1830889Notes

Reaction equation

HRID 1830889 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].[Cu](C#N)[C:12]#[N:13].N>CN(C=O)C>[C:12]([C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8])#[N:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 18085-BromonicotinamideHCID 178418260HCID 178418260, compound

Product 1

HCID 220497915-CyanonicotinamideYield 16.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

5-Bromonicotinamide (905 mg) and copper cyanide (630 mg) were suspended in DMF (15 ml) and the mixture was stirred at 140° C. for 24 hrs. Aqueous ammonia was added to the reaction mixture at room temperature and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent, methanol:ethyl acetate=1:10) for purification to give the title compound (110 mg) as a colorless powder.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was subjected to silica gel column chromatography (eluent, methanol:ethyl acetate=1:10) for purification

Sources & evidence

ORD record
ord-2c451a5a9ee546ffb4d39368ddded883
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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