Hydrochloric Acid → Ethyl 6-hydroxynicotinate

HRID 2080004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080004
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.Cl.C(=O)(O)[O-].[Na+].[CH2:17](O)[CH3:18]>>[CH2:17]([O:7][C:6]([C:5]1[CH:9]=[CH:10][C:2](=[O:1])[NH:3][CH:4]=1)=[O:8])[CH3:18]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 178418479HCID 178418479, Verbindung

Produkt 1

HCID 295861Ethyl 6-hydroxynicotinateAusbeute 65 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a suspension of 6-hydroxy-nicotinic acid (5.00 g, 35.9 mmol) in ethanol (60 mL) was added 1N hydrochloric acid (20 mL), which was then stirred at 110° C. for 3 hours. The reaction solution was cooled to 0° C., then, an aqueous solution of saturated sodium bicarbonate was added, the solution was extracted with ethyl acetate and tetrahydrofuran, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (ethyl acetate), and the title compound (3.90 g, 23.3 mmol, 65%) was obtained as a white solid.

Aufarbeitung

  1. temperatureThe reaction solution was cooled to 0° C.
  2. extractionthe solution was extracted with ethyl acetate and tetrahydrofuran
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f3786a8e0e5d4e75956a0988b796ee80
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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