Citric Acid → Methyl 5-methoxypyridine-2-carboxylate

HRID 2080697Notes

Reaction equation

HRID 2080697 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:11]C)=[O:9])=[N:6][CH:7]=1.[C:13](=O)([O-])[O-:14].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O.CO>[CH3:13][O:14][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 10986675Ethyl 5-fluoropyridine-2-carboxylate

Product 1

HCID 14282457Methyl 5-methoxypyridine-2-carboxylateYield 47.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

100 mg of ethyl 5-fluoropyridine-2-carboxylate obtained from Reference Example 18 (step 2) was dissolved in 1 ml of dimethylformamide and 1 ml of methanol, and 163 mg of potassium carbonate was added to it and stirred under heat at 90° C. for 40 minutes. 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, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 46.5 mg of methyl 5-methoxypyridine-2-carboxylate 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
  5. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-09d2e94059914fe2a40620aa7e2f3f2d
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

Loading…