Potassium Hydroxide → 4-(Methoxycarbonyl)pyridine-2-carboxylic acid

HRID 2064265Notes

Reaction equation

HRID 2064265 reaction equation
[OH-].[K+].[N:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:4]=1[C:13]([O:15]C)=[O:14]>CO>[CH3:12][O:11][C:9]([C:6]1[CH:7]=[CH:8][N:3]=[C:4]([C:13]([OH:15])=[O:14])[CH:5]=1)=[O:10]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 254545Dimethyl pyridine-2,4-dicarboxylate

Product 1

HCID 133537524-(Methoxycarbonyl)pyridine-2-carboxylic acidYield 100.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methanol (800 mL), potassium hydroxide (44 g, 0.95 mol) and dimethyl pyridine-2,4-dicarboxylate (ChemPacific) (156 g, 0.79 mol) was refluxed for 0.5 hours and then evaporated in vacuo to afford 4-(methoxycarbonyl)picolinic acid (144 g) as a yellow solid.

Workup

  1. temperaturewas refluxed for 0.5 hours
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb9f6bf5254a49ac94949f4fd4c27672
Source dataset
uspto-grants-2012_10
Patent number
US08288405B2

Reaction notes

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