imidazo[1,2-a]pyridine-6-carboxamide → imidazo[1,2-a]pyridine-6-carbonitrile

HRID 1607303Notes

Reaction equation

HRID 1607303 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH:10]=[CH:11][N:12]=2)[CH:9]=1)(=O)[NH2:2]>P(Cl)(Cl)(Cl)=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH:10]=[CH:11][N:12]=2)[CH:9]=1)#[N:2]

Participants

3

Reactant 1

HCID 326954imidazo[1,2-a]pyridine-6-carboxamide

Product 1

HCID 2764471imidazo[1,2-a]pyridine-6-carbonitrileYield 86.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 2.6 g of 6-carbamoylimidazo[1,2-a]pyridine and 30 ml of phosphorus oxychloride is heated under reflux for 16 hours. The excess phosphorus oxychloride is removed under reduced pressure and the residue is poured onto ice. The mixture is neutralized with sodium carbonate and extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then evaporated off under reduced pressure to give 2.0 g of the above-identified compound as colorless crystals.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 16 hours
  3. customThe excess phosphorus oxychloride is removed under reduced pressure
  4. additionthe residue is poured onto ice
  5. extractionextracted with ethyl acetate
  6. washThe organic layer is washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent is then evaporated off under reduced pressure

Sources & evidence

ORD record
ord-b748106a476c494095cb914110026ee8
Source dataset
uspto-grants-1989_09
Patent number
US04864022

Reaction notes

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