Hydrazine hydrate (1:1) → HCID 135519368, Verbindung

HRID 1867567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867567
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7]([C:13]([OH:15])=[O:14])=[C:6]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:5]2=O.O.[NH2:26][NH2:27]>C(O)C.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]([OH:8])=[C:4]([C:5]2[C:6]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[C:7]([C:13]([OH:15])=[O:14])[NH:26][N:27]=2)[CH:3]=1

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 11416722HCID 11416722, Verbindung

Produkt 1

HCID 135519368HCID 135519368, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 516892Sodium BicarbonateKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

6-Chloro-7-hydroxy-3-(4methoxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid (1 eq) was taken up in ethanol and hydrazine hydrate (3 eq) was added. To aid dissolution a few drops of NaHCO3 (aq) was added, and then all was heated at 70° C. under nitrogen for 2 hours. The solution was cooled to room temperature and concentrated in vacuo to a brown oil. This was partitioned between 1MHCl(aq) and diethyl ether. The organic phases were combined, washed with 1MHCl(aq), dried over MgSO4, filtered and concentrated in vacuo to give 5-(5-chloro-2,4dihydroxy-phenyl)-4-(4-methoxy-phenyl)-2H-pyrazole-3-carboxylic acid as a yellow foam.

Aufarbeitung

  1. additionwas added
  2. temperatureThe solution was cooled to room temperature
  3. concentrationconcentrated in vacuo to a brown oil
  4. customThis was partitioned between 1MHCl(aq) and diethyl ether
  5. washwashed with 1MHCl(aq)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e28302da3592433696f6ec7d8b64caf9
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632855B2

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