Sodium Hydroxide → 3-(Pyridin-3-yl)benzoic acid

HRID 2201997Notes

Reaction equation

HRID 2201997 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12]C)=[O:11])[CH:2]=1.[OH-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([OH:12])=[O:11])[CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4133188Methyl 3-(3-pyridinyl)benzoate

Product 1

HCID 27955753-(Pyridin-3-yl)benzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(pyridin-3-yl)benzoate (450 mg, 2.1 mmol) in MeOH (5 mL) was added aqueous of NaOH (1.5 mL, 0.4M). The mixture was stirred at room temperature for 2 h then reaction solution was concentrated and the resulting residue dissolved in water and adjusted pH to 5-6 with 2N HCl. Extracted was then performed using EtOAc with the organic layer dried and concentrated to give the target product which was used without further purification (600 mg, Yield 90%). LCMS (m/z): 200.1 (M+1).

Workup

  1. customreaction solution
  2. concentrationwas concentrated
  3. dissolutionthe resulting residue dissolved in water
  4. extractionExtracted
  5. customdried
  6. concentrationconcentrated
  7. customto give the target product which
  8. customwas used without further purification (600 mg, Yield 90%)

Sources & evidence

ORD record
ord-ffb189424b5c42b589ff62ad9ae906df
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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