Hydrochloric Acid → 5-(Ethoxycarbonyl)pyridine-3-carboxylic acid

HRID 1719474Notes

Reaction equation

HRID 1719474 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([O:9]CC)=[O:8])[CH:4]=[C:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:2]=1.Cl>C(O)C.[OH-].[K+]>[C:12]([C:3]1[CH:4]=[C:5]([C:7]([OH:9])=[O:8])[CH:6]=[N:1][CH:2]=1)([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 78340Diethyl pyridine-3,5-dicarboxylate

Product 1

HCID 12144465-(Ethoxycarbonyl)pyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

To a solution of 10 g (0.045 mol) of diethyl 3,5-pyridinedicarboxylate in 75 ml of ethyl alcohol, 25 ml of 2N alcoholic KOH were added while stirring. Stirring was continued for 1/2 hour at room temperature. To the mixture, 12.5 ml of 4N HCl were added while stirring. The solid which separated was filtered and washed with alcohol. The combined filtrate and washings were distilled on rotovap and the residue was washed with water, filtered and crystallized from ethanol. Yield 7.5 g (86%), m.p. 180°-182° C., NMR (CDCl3 /DMSO-d6) δ 10.56 (bs, 1H, COOH), 9.26 (d, 2H, J=2 Hz, C2 and C6 pyridine protons), 8.75 (t, 1H, J=2 Hz, C4 pyridine protons), 4.4 (q, 2H, J=7 Hz, O--CH2), 1.42 (t, 3H, J=7 Hz, CH3).

Workup

  1. stirringStirring
  2. stirringwhile stirring
  3. customThe solid which separated
  4. filtrationwas filtered
  5. washwashed with alcohol
  6. distillationThe combined filtrate and washings were distilled on rotovap
  7. washthe residue was washed with water
  8. filtrationfiltered
  9. customcrystallized from ethanol

Sources & evidence

ORD record
ord-eaf46ecaa540494d880e9036442b7606
Source dataset
uspto-grants-1985_09
Patent number
US04540564

Reaction notes

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