6-Carbamoylpyridine-2-carboxylic acid → 6-Cyanopyridine-2-carboxylic acid

HRID 1397290Notes

Reaction equation

HRID 1397290 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][CH:5]=1)(=O)[NH2:2]>P(Cl)(Cl)(Cl)=O>[C:1]([C:4]1[N:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][CH:5]=1)#[N:2]

Participants

3

Reactant 1

HCID 186766986-Carbamoylpyridine-2-carboxylic acid

Product 1

HCID 212530396-Cyanopyridine-2-carboxylic acidYield 56.3%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

6-Carbamoylpicolinic acid (1.0 g, 6.0 mmol) was taken in phosphorus oxychloride (20 mL) and heated to reflux for 4 h. Excess POCl3 was removed under reduced pressure and the residue was quenched with ice water. The organic product was extracted with EtOAc and the solvent was removed under reduced pressure to afford 6-cyanopicolinic acid (500 mg, yield 56%), which was carried through without further purification. 1H NMR (300 MHz, DMSO-d6) δ 8.31-8.28 (m, 2H), 8.26-8.21 (m, 1H). MS (ESI) m/z: Calculated for C7H4N2O2: 148.03. found: 147.2 (M−H)−.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customExcess POCl3 was removed under reduced pressure
  4. customthe residue was quenched with ice water
  5. extractionThe organic product was extracted with EtOAc
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4526c5e2257a4ede8c9ab7d6bc4fa56e
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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