Sulfuric Acid → Dimethyl pyridine-3,5-dicarboxylate

HRID 1698359Notes

Reaction equation

HRID 1698359 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[CH:4]=C(C(O)=O)[CH:2]=1.OS(O)(=O)=O.[C:18]([O:21][CH2:22]C)(=[O:20])[CH3:19].[CH3:24]CCCCC>CO>[CH3:24][O:9][C:7]([C:5]1[CH:6]=[N:1][CH:2]=[C:19]([C:18]([O:21][CH3:22])=[O:20])[CH:4]=1)=[O:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 103663,5-Pyridinedicarboxylic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 78339Dimethyl pyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,5-Pyridinedicarboxylic acid (1.5 g, 63 mmol) and conc. H2SO4 (0.9 mL) in MeOH (15 mL) are heated in a microwave oven at 120° C. for 2 h. The solvent is evaporated to give a residue with is partitioned between ethyl acetate and sat. aq. NaHCO3. The organic phase is washed with brine, dried over Na2SO4, filtered and evaporated to give a light yellow solid. MS (LC-MS): 196 [M+H]+ TLC, Rf (ethyl acetate/hexane 1:1)=0.56.

Workup

  1. customThe solvent is evaporated
  2. customto give a residue
  3. customwith is partitioned between ethyl acetate and sat. aq. NaHCO3
  4. washThe organic phase is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a light yellow solid

Sources & evidence

ORD record
ord-072ae52052a6444a90760a90aefb75ce
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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