Hydrazine → 4-Bromopyridazine-3,6-diol

HRID 1369425

Reaktionsgleichung

Reaktionsgleichung von HRID 1369425
O.[NH2:2][NH2:3].[Br:4][C:5]1[C:6](O[C:9](=[O:11])[CH:10]=1)=[O:7].NN>C1COCC1>[Br:4][C:5]1[C:6](=[O:7])[NH:2][NH:3][C:9](=[O:11])[CH:10]=1

Komponenten

5

Edukt 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 800273-Bromo-2,5-furandione

Produkt 1

HCID 2549424-Bromopyridazine-3,6-diolAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Hydrazine hydrate (28 ml, 576 mmol) was added dropwise to a stirred solution of bromomaleic anhydride (100 g, 565 mmol) in THF (1l) cooled in an ice-bath so that the internal temperature did not exceed 10° C. After complete addition of the hydrazine the mixture was refluxed for 18 h. Solvent was removed by evaporation and the residues were dried by azeotroping with toluene. The residue was triturated and washed with diethyl ether to give the title compound as an orange solid (83 g, 77%). 1H NMR (250 MHz, d6-DMSO) δ7.68 (1H, br s). MS (ES+) m/e 193 [MH]+, 191 [MH]+. This material was used without further purification.

Aufarbeitung

  1. temperaturecooled in an ice-bath so that the internal temperature
  2. customdid not exceed 10° C
  3. temperaturewas refluxed for 18 h
  4. customSolvent was removed by evaporation
  5. customthe residues were dried
  6. customby azeotroping with toluene
  7. customThe residue was triturated
  8. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-79cd024ef57846208ae3a3654c979b16
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06579875B1

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