Sodium Acetate → 5-(2-Chloroethyl)-pyridinedicarboxylic acid, dimethyl ester

HRID 1741629Notes

Reaction equation

HRID 1741629 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:3]=1[CH2:16][CH2:17][Cl:18].C([O-])(=O)C.[Na+]>[Pd].CO>[Cl:18][CH2:17][CH2:16][C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]([C:8]([O:10][CH3:11])=[O:9])=[N:7][CH:2]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 19958230Dimethyl 5-(2-chloroethyl)-6-chloro-2,3-pyridinedicarboxylate

Product 1

HCID 867480385-(2-Chloroethyl)-pyridinedicarboxylic acid, dimethyl esterYield 56.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 18 g of 6-chloro-5-(2-chloroethyl)pyridine-2,3-dicarboxylic acid, dimethyl ester, 1 g of 10% palladium on carbon, and 7 g of sodium acetate in 100 mL methanol is shaken in a hydrogenation apparatus under 15 psi for 23 hours. The reaction is then filtered through celite, and the catalyst is washed with a little methanol. The combined filtrates are concentrated in vacuo, and the residue is partitioned between methylene chloride and water. The organic phase is washed with saturated bicarbonate, dried, and concentrated in vacuo. The residue is chromatographed on silica gel using hexane-ethyl acetate mixtures to afford 8.9 g of the desired product as an oil.

Workup

  1. filtrationThe reaction is then filtered through celite
  2. washthe catalyst is washed with a little methanol
  3. concentrationThe combined filtrates are concentrated in vacuo
  4. customthe residue is partitioned between methylene chloride and water
  5. washThe organic phase is washed with saturated bicarbonate
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-b3ba293bc49641828c2517ce6f066dc0
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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