Acetic Acid → 6-Methyl-3-(1H-pyrazol-1-yl)picolinic acid

HRID 61089Notes

Reaction equation

HRID 61089 reaction equation
[CH3:1][C:2]1[N:7]=C(C#N)[C:5]([N:10]2[CH:14]=[CH:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:17][C:18]([OH:20])=[O:19]>CO>[CH3:1][C:2]1[N:7]=[C:17]([C:18]([OH:20])=[O:19])[C:5]([N:10]2[CH:14]=[CH:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 1177281526-Methyl-3-(1H-pyrazol-1-yl)picolinonitrile

Product 1

HCID 593636726-Methyl-3-(1H-pyrazol-1-yl)picolinic acidYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

6-Methyl-3-(1H-pyrazol-1-yl)picolinonitrile (0.60 g, 3.26 mmol) and NaOH (1.37 g, 34.2 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 (0.62 g, 94%). MS (ESI) 204 (M+H).

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-4705ada6d96d46f0b0f74ced5f46e5bb
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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