Citric Acid → 5-fluoropyridine-2-carboxylic Acid

HRID 2080696Notes

Reaction equation

HRID 2080696 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12]CC)=[O:11])=[N:8][CH:9]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 10986675Ethyl 5-fluoropyridine-2-carboxylate

Product 1

HCID 27628765-fluoropyridine-2-carboxylic AcidYield 111.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.4 ml of aqueous 2.5 N sodium hydroxide solution was added to a solution of 0.44 g of ethyl 5-fluoropyridine-2-carboxylate in 5 ml of tetrahydrofuran and 2 ml of methanol, and stirred at room temperature for 15 minutes. This was neutralized with aqueous 10% citric acid solution, extracted with ethyl acetate, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure to obtain 0.41 g of the entitled compound as a white crystal.

Workup

  1. extractionextracted with ethyl acetate
  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-746d6581b7c44525a377a0ca6b6c8565
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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