Sodium Hydroxide → 2-(4-Fluorophenyl)pyridine-4-carboxylic acid

HRID 602382Notes

Reaction equation

HRID 602382 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11]([O:13]C)=[O:12])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11]([OH:13])=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66732391Methyl 2-(4-fluorophenyl)pyridine-4-carboxylate

Product 1

HCID 463131162-(4-Fluorophenyl)pyridine-4-carboxylic acidYield 51.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-(4-fluorophenyl)isonicotinate (278 mg, 1.20 mmol) was dissolved in methanol (2 mL) and the solution was added with 2 mol/L aqueous sodium hydroxide solution (2 mL, 4.0 mmol), followed by stirring at room temperature overnight. The solvent was evaporated under reduced pressure and the obtained reaction mixture was dissolved in water. The solution was washed with ethyl acetate, then was added with 1 mol/L hydrochloric acid, and the obtained crystal was collected by filtration to obtain 2-(4-fluorophenyl)isonicotinic acid (134 mg, 51%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained reaction mixture
  3. washThe solution was washed with ethyl acetate
  4. additionwas added with 1 mol/L hydrochloric acid
  5. filtrationthe obtained crystal was collected by filtration

Sources & evidence

ORD record
ord-16046aadcd824ba8aa7e7e0bcaf64c8d
Source dataset
uspto-grants-2011_03
Patent number
US07906522B2

Reaction notes

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