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

HRID 1633216Notes

Reaction equation

HRID 1633216 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]([O:14]CC)=[O:13])[CH:11]=1)=[O:5])[CH3:2].Cl>C(O)C.[OH-].[K+]>[C:4]([C:6]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[N:8][CH:7]=1)([O:3][CH2:1][CH3:2])=[O:5]

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 compound 6 in 75 ml of ethyl alcohol, 25 ml of 2N alcoholic KOH was added while stirring. Stirring was continued for 1/2 hr at room temperature. To the mixture 12.5 ml of 4N HCl was added while stirring. The solid 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°, NMR (CDCl3 /DMSO-d6) δ10.56 (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 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-d5034d0062084dd58bb64c92ef9ba1dd
Source dataset
uspto-grants-1984_10
Patent number
US04479932

Reaction notes

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