Water → 5-phenylpyridine-2-carboxylic Acid

HRID 1177971Notes

Reaction equation

HRID 1177971 reaction equation
[OH2:1].[OH-:2].[Na+].[C:4]1([C:10]2[CH:11]=[CH:12][C:13]([C:16]#N)=[N:14][CH:15]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[C:4]1([C:10]2[CH:11]=[CH:12][C:13]([C:16]([OH:2])=[O:1])=[N:14][CH:15]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 9352765-Phenylpyridine-2-carbonitrile

Product 1

HCID 27628705-phenylpyridine-2-carboxylic AcidYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Water (1 mL) and NaOH (56 mg, 1.41 mmol) were added to a stirred solution of 5-phenyl-pyridine-2-carbonitrile (112 mg, 0.56 mmol) in ethanol at room temperature. The resulting mixture was heated at reflux temperature for 3 hours. The EtOH was evaporated, and the mixture was diluted with water (2 mL), acidified with citric acid solution and the product was extracted using EtOAc. The organic layer was washed with saturated brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford 30 mg (27% yield) of 5-phenyl-pyridine-2-carboxylic acid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux temperature for 3 hours
  3. customThe EtOH was evaporated
  4. additionthe mixture was diluted with water (2 mL)
  5. extractionthe product was extracted
  6. washThe organic layer was washed with saturated brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d91f01daccec44579e53ad05ca7e830d
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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