Hydrochloric Acid → 5-(3-Methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylic acid

HRID 399800

Reaktionsgleichung

Reaktionsgleichung von HRID 399800
[OH:1][N:2]=[C:3]([NH2:5])[CH3:4].[H-].[Na+].C[O:9][C:10]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18](OC)=O)[CH:17]=1)=[O:11].Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:4][C:3]1[N:5]=[C:18]([C:16]2[CH:17]=[C:12]([C:10]([OH:11])=[O:9])[CH:13]=[N:14][CH:15]=2)[O:1][N:2]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 30926N-HydroxyacetamidineHCID 78339Dimethyl pyridine-3,5-dicarboxylate

Produkt 1

HCID 189454415-(3-Methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylic acidAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 1-(hydroxyimino)ethylamine (7.4 g) in dry tetrahydrofuran (450 ml) was added sodium hydride (3.7 g, 60% in mineral oil) carefully. The mixture was stirred at room temperature for 15 minutes, and refluxed for 30 minutes. To this mixture was added 3,5-bis(methoxycarbonyl)pyridine (15 g), and the mixture was refluxed for 3 hours. After being cooled to room temperature, the reaction mixture was poured into a mixture of ethyl acetate (200 ml) and water (200 ml) under stirring. The aqueous layer was adjusted to pH 3.5 with 10% hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and dried in vacuo to afford 5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylic acid (5.04 g).

Aufarbeitung

  1. temperaturerefluxed for 30 minutes
  2. temperaturethe mixture was refluxed for 3 hours
  3. temperatureAfter being cooled to room temperature
  4. stirringunder stirring
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-10620e7650ea4b268785acb95674cca6
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05824691

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