Sodium Hydroxide → 4-Pyridin-3-yl-benzoic acid

HRID 1677134Notes

Reaction equation

HRID 1677134 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:16])=[O:2])=[CH:5][CH:6]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4133187Methyl 4-pyridin-3-ylbenzoate

Product 1

HCID 15152444-Pyridin-3-yl-benzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Procedure J′: 648 mg of 4-Pyridin-3-yl-benzoic acid methyl ester (3.04 mmol) is dissolved in 15 ml of MeOH and 10 ml of 1N NaOH is added. The reaction mixture is stirred at 50° C. for 30 min and room temperature for overnight. MeOH is removed in vacuo and the residue is acidified to pH=4.0 by 1N HCl. Crystals are filtered and washed by water and dried to give 578 mg of 4-pyridin-3-yl-benzoic acid (96%). 1H-NMR (DMSO): 13.1 (br, 1H), 8.98 (m, 1H), 8.64 (m, 1H), 8.17 (m, 1H), 8.07 (d, 2H, J=8.0 Hz), 7.89 (d, 2H, J=8.0 Hz), 7.57 (m, 1H).

Workup

  1. customMeOH is removed in vacuo
  2. filtrationCrystals are filtered
  3. washwashed by water
  4. customdried

Sources & evidence

ORD record
ord-8490823a386f4f0d8516719eed131ea2
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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