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

HRID 1199549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199549
[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]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 783403,5-Pyridinedicarboxylic acid, 3,5-diethyl ester

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14797Potassium HydroxideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-21a3d55f38554728b278d66a34fdad28
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04900837

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