Citric Acid → 5-Methoxypyridine-2-carboxylic acid

HRID 2080698Notes

Reaction equation

HRID 2080698 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([O:11]C)=[O:10])=[N:7][CH:8]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=[O:10])=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 14282457Methyl 5-methoxypyridine-2-carboxylate

Product 1

HCID 119589395-Methoxypyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The obtained ester compound was dissolved in 0.5 ml of methanol and 0.5 ml of tetrahydrofuran, and 0.52 ml of aqueous 1 N sodium hydroxide solution was added to it, and stirred at room temperature for 2 hours. This was neutralized with aqueous 10% citric acid solution, extracted with chloroform, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure to obtain 17.2 mg of the entitled compound as a white crystal.

Workup

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with saturated saline water
  3. customAfter dried
  4. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-268dac802bb44f3b8c5cbe34513c3634
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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