6-Amino-3-chloropyridazine → Ethyl 7-chloro-4-oxo-4H-pyrimido[1,2-b]pyridazine-3-carboxylate

HRID 224227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 224227
[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1.C([O:11][CH:12]=[C:13]([C:19]([O-])=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>C1(OC2C=CC=CC=2)C=CC=CC=1.CCCCCC>[CH2:17]([O:16][C:14]([C:13]1[C:12](=[O:11])[N:4]2[N:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]2=[N:8][CH:19]=1)=[O:15])[CH3:18]

Komponenten

5

Edukt 2

HCID 216436-Amino-3-chloropyridazineHCID 858292113-Ethoxy-2-ethoxycarbonylprop-2-enoate

Produkt 1

HCID 13437596Ethyl 7-chloro-4-oxo-4H-pyrimido[1,2-b]pyridazine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7583Diphenyl EtherLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A mixture of 3-chloro-6-aminopyridazine [J. Druey et al., Helv. Chim. Acta., 37, 121 (1954)] (8.20 g, 63.56 m mol) and ethyl ethoxymethylenemalonate (15.0 g, 69.4 m mol) in diphenyl ether (70 ml) was heated to distil out ethanol produced. After cooling, the mixture was diluted with n-hexane (300 ml) to precipitate the crude title product, which was dissolved in chloroform (200 ml), treated with a small amount of carbon and evaporated under reduced pressure to 50 ml. The residual solution was diluted with n-hexane (200 ml) to precipitate pure title product. Yield, 7.73 g (56%), M.p. 149°-152° C.

Aufarbeitung

  1. temperaturewas heated
  2. customto distil out ethanol
  3. customproduced
  4. temperatureAfter cooling
  5. customto precipitate the crude title product, which
  6. dissolutionwas dissolved in chloroform (200 ml)
  7. additiontreated with a small amount of carbon
  8. customevaporated under reduced pressure to 50 ml
  9. additionThe residual solution was diluted with n-hexane (200 ml)
  10. customto precipitate pure title product
  11. customYield

Quellen und Nachweise

ORD-Eintrag
ord-0e1c96b5cbad4132a04e817a666ebd83
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04231928

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