Sulfuric Acid → Ethyl 3-hydroxyisonicotinate

HRID 16703

Reaktionsgleichung

Reaktionsgleichung von HRID 16703
N[C:2]1[CH:12]=[N:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(=O)(=O)(O)[OH:14].N([O-])=O.[Na+].C(=O)([O-])O.[Na+]>O>[OH:14][C:2]1[CH:12]=[N:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 2736365Ethyl 3-AminoisonicotinateHCID 23668193Sodium Nitrite

Produkt 1

HCID 12326192Ethyl 3-hydroxyisonicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Versuchsvorschrift

Ethyl 3-aminoisonicotinate (5.55 g) is suspended in water (70 ml), and thereto added conc. sulfuric acid (4.0 ml). The reaction solution is cooled with ice, and a solution of sodium nitrite (2.79 g) in water (30 ml) is added dropwise thereto. The reaction solution is stirred under the same cooling conditions for 20 minutes and then at 90° C. for 80 minutes. The reaction solution is diluted with water (100 ml) and the solution is adjusted to pH 8 to 9 by addition of saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer is dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1) to give ethyl 3-hydroxyisonicotinate (2.64 g).

Aufarbeitung

  1. temperatureThe reaction solution is cooled with ice
  2. temperaturesame cooling conditions for 20 minutes
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-3f5f977eb2d149f0905420bb1858210a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737161B2

Verknüpfte Notizen

Wird geladen…