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

HRID 1633216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633216
[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]

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 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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d5034d0062084dd58bb64c92ef9ba1dd
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04479932

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