Sodium Hydroxide → 3-(Pyridin-2-yl)benzoic acid

HRID 2201989Notes

Reaction equation

HRID 2201989 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12]C)=[O:11].[OH-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3364101Methyl 3-(pyridin-2-yl)benzoate

Product 1

HCID 51525923-(Pyridin-2-yl)benzoic acidYield 161.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(pyridin-2-yl)benzoate (300 mg, 1.40 mmol) in MeOH (3 mL) was added aqueous NaOH (1 mL, 0.4M). The mixture was stirred at room temperature for 3 h. The reaction solution was concentrated and the residue dissolved in water and adjust pH to 5-6 with 2N of HCl. The solution was extracted with EtOAc (3×20 mL) and the combined organic layers concentrated to give the desired crude product (450 mg, Yield 90%) which was used in the next step without further purification. LCMS (m/z): 200.1 (M+1).

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe residue dissolved in water
  3. extractionThe solution was extracted with EtOAc (3×20 mL)
  4. concentrationthe combined organic layers concentrated

Sources & evidence

ORD record
ord-57a2233f5198462bbf33f1ac042fb998
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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