Acetic Acid → 6'-Methyl-2,3'-bipyridine-2'-carboxylic acid

HRID 61093Notes

Reaction equation

HRID 61093 reaction equation
[CH3:1][C:2]1[N:7]=C(C#N)[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:18][C:19]([OH:21])=[O:20]>CO>[CH3:1][C:2]1[N:7]=[C:18]([C:19]([OH:21])=[O:20])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 593637166'-Methyl-2,3'-bipyridine-2'-carbonitrile

Product 1

HCID 593637356'-Methyl-2,3'-bipyridine-2'-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

6′-Methyl-[2,3′-bipyridine]-2′-carbonitrile (0.87 g, 4.46 mmol) and NaOH (1.87 g, 46.8 mmol) were dissolved in methanol (3 mL) and stirred at reflux overnight. The reaction was cooled to rt, diluted with more methanol (5 ml), and acidified with AcOH to pH 4-5. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% DCM/EtOAc) to yield the title compound as a clear oil (0.9 g, 94%).

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was removed in vacuo
  3. customto obtain the crude which
  4. customwas purified by silica gel chromatography (0˜100% DCM/EtOAc)

Sources & evidence

ORD record
ord-7989130023d04570a080c64d4377acf5
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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