Hydrochloric Acid → 6-Chloro-4-ethoxy-pyridazine-3-carboxylic acid ethyl ester

HRID 1244255

Reaktionsgleichung

Reaktionsgleichung von HRID 1244255
[O-:1][CH2:2][CH3:3].[Na+].[CH2:5]([O:7][C:8]([C:10]1[N:11]=[N:12][C:13]([Cl:17])=[CH:14][C:15]=1Cl)=[O:9])[CH3:6].Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH2:5]([O:7][C:8]([C:10]1[N:11]=[N:12][C:13]([Cl:17])=[CH:14][C:15]=1[O:1][CH2:2][CH3:3])=[O:9])[CH3:6]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylate

Produkt 1

HCID 859613046-Chloro-4-ethoxy-pyridazine-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium ethoxide (1.16 g, 17 mmol) is added to a stirred solution of 4,6-dichloropyridazine-3-carboxylic acid ethyl ester (3.73 g, 17 mmol) in THF (45 mL) cooled to 0° C. The reaction mixture is stirred at room temperature overnight and then poured into 1N HCl (20 mL). The resulting solution is then neutralized with saturated NaHCO3. EtOAc (20 mL) is added and the layers are separated. The aqueous layer is extracted twice with EtOAc (20 mL) and the combined extracts are washed with brine (25 mL), dried (Na2SO4), and evaporated. The residue is then purified by flash column chromatography (silica gel, eluted with 2:1 Hexane, EtOAc) to give the title product as a white solid. H1 NMR δ (CDCl3) 7.02 (s, 1H), 4.47 (q, 2H, J=7.2 Hz), 4.19 (q, 2H, J=7.2 Hz), 1.50 (t, 3H, J=7.2 Hz), 1.41 (t, 3H, J=7.2 Hz).

Aufarbeitung

  1. customthe layers are separated
  2. extractionThe aqueous layer is extracted twice with EtOAc (20 mL)
  3. washthe combined extracts are washed with brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue is then purified by flash column chromatography (silica gel, eluted with 2:1 Hexane, EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-368648d478334543afe2f74ff5c032db
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122546B2

Verknüpfte Notizen

Wird geladen…