Hydrazine hydrate (1:1) → 4-Phenylpyridazine-3,6-diol

HRID 383556

Reaktionsgleichung

Reaktionsgleichung von HRID 383556
[C:1]1([C:7]2[C:8](=O)[O:9][C:10](=[O:12])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:15][NH2:16]>C(O)C>[C:1]1([C:7]2[C:8](=[O:9])[NH:15][NH:16][C:10](=[O:12])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 99174Phenylmaleic anhydride

Produkt 1

HCID 136348344-Phenylpyridazine-3,6-diolAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4.0 g (23 mmole) of 3-phenylfuran-2,5-dione was added to a 100 ml single-necked round bottom flask followed by 2.9 g (27.6 mmole) of hydrazine monohydrate and then 20 ml of reagent grade ethanol (95%). The flask was fitted with a reflux condenser and the reaction mixture was heated to reflux in an oil bath at 110 degree (temperature of oil bath) and stirred for 2 h. The flask was then removed from the oil bath and the reaction mixture cooled to ambient temperature. The stir bar was removed and the solvent was evaporated in vacuo in a water bath at 45 degree. The residue was then treated with 50 ml of Milli-Q water and stirred for 10 minutes to give a suspension. The precipitate was collected by filtering, washed with 100 ml of Milli-Q water, and dried over a medium frit sintered glass funnel in vacuo to give 3.9 g of white solid. Yield, 91%, confirmed by ESI-MS. ESI-MS: m/z 189.2 (M+H).

Aufarbeitung

  1. customThe flask was fitted with a reflux condenser
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux in an oil bath at 110 degree (temperature of oil bath)
  4. customThe flask was then removed from the oil bath
  5. customThe stir bar was removed
  6. customthe solvent was evaporated in vacuo in a water bath at 45 degree
  7. additionThe residue was then treated with 50 ml of Milli-Q water
  8. stirringstirred for 10 minutes
  9. customto give a suspension
  10. customThe precipitate was collected
  11. filtrationby filtering
  12. washwashed with 100 ml of Milli-Q water
  13. customdried over a medium frit sintered glass funnel in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cc5e023de5d343848ce315987801a93d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367672B2

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