Water → 6-(Benzyloxy)pyridine-3-carboxylic acid

HRID 1177903Notes

Reaction equation

HRID 1177903 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#N)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:17].[Na+].[OH2:19]>CCO>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]([OH:19])=[O:17])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 247001066-(Benzyloxy)pyridine-3-carbonitrile

Product 1

HCID 2772386-(Benzyloxy)pyridine-3-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 6-benzyloxy-nicotinonitrile (100 mg, 0.47 mmol) in a mixture of EtOH (5 mL) and water (5 mL), was added NaOH (95.1 mg, 2.3 mmol) and the resulting mixture was stirred at 90° C. for 20 hrs. The mixture was evaporated under reduced pressure. The residue was diluted with cold water, adjusted the pH to 3 and extracted with EtOAc. The organic layer was washed with saturated brine solution and dried over Na2SO4. The organic layer was then concentrated under reduced pressure to afford 105 mg (96% yield) of 6-benzyloxy-nicotinic acid.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. additionThe residue was diluted with cold water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationThe organic layer was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-ccb10e5e37cd4352855a1a32139f9d51
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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