Water → 4-Pyridin-3-yl-benzoic acid

HRID 1745009Notes

Reaction equation

HRID 1745009 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[CH:2]=1.[O-:14][Mn](=O)(=O)=O.[K+].[OH2:20]>N1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([OH:14])=[O:20])=[CH:11][CH:12]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 41331893-(4-methylphenyl)pyridine

Product 1

HCID 15152444-Pyridin-3-yl-benzoic acidYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 4-tolylboronic acid (38 g, 0.28 mol), 3-bromopyridine (44 g, 0.28 mol), Na2CO3 (200 g) in toluene (500 ml) and water (500 ml) was added Pd(PPh3)4 (16 g, 0.014 mol), and refluxed for 16 h. The reaction mixture was cooled, and the separated organic layer was washed with water and brine, and dried. The solvent was removed to give 4-(3-pyridyl)toluene (42 g, 90%). To a mixture of 4-(3-pyridyl)toluene (35 g, 0.207 mol) in pyridine (400 ml) and water (400 ml) was added KMnO4 (163 g, 1.03 mol) in portions and refluxed for 12 h. The reaction mixture was filtered through celite and acidified with conc. HCl. The product was washed with water and dried to give 4-(3-pyridyl)benzoic acid (32 g, 76%) as a white solid. To a mixture of 4-(3-pyridyl)benzoic acid (22 g, 0.11 mol) in THF (2.51), mCPBA (152 g, 0.44 mol, 50%) was added and stirred at RT for 12 h. The solid was filtered, and washed with THF to give 4-(1-oxido-3-pyridinyl)benzoic acid (20 g, 86%).

Workup

  1. temperaturerefluxed for 12 h
  2. filtrationThe reaction mixture was filtered through celite
  3. washThe product was washed with water
  4. customdried

Sources & evidence

ORD record
ord-e580a1f54ccf4d96867088e07d21f20e
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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