4-Hydrazinobenzoic acid → 4-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoic acid

HRID 1817056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1817056
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[N:9][C:8]([C:12]([O-:14])=O)=[C:7]2O.[NH:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)[NH2:17]>S(Cl)(Cl)=O.C(O)C>[F:1][C:2]1[C:11]2[N:10]=[N:9][C:8]3[C:12](=[O:14])[N:16]([C:18]4[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:25][CH:26]=4)[NH:17][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 120894-Hydrazinobenzoic acidHCID 178524933HCID 178524933, Verbindung

Produkt 1

HCID 589748824-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

Crude 8-Fluoro-4-hydroxycinnoline-3-carboxylate from the previous stage (1.00 g, 4.95 mmol) was dissolved in thionyl chloride (50 ml). The solution was heated to reflux for 2-3 h until no further gas evolution was observed. The reaction mixture was cooled to room temperature and excess thionyl chloride was removed under vacuum. The crude intermediate was azeotroped with toluene (3×25 ml). A dark brown solid was obtained, which was taken up in ethanol (25 ml). 4-Hydrazinobenzoic acid (640 mg, 4.21 mmol) was added and the mixture was stirred at room temperature overnight. The solids were collected by filtration, slurried in 1 M HCl (100 ml), filtered, washed with hexane (50 ml) and dried under vacuum. A brown solid was obtained (890 mg of crude product). LCMS: m/z [M+H]+ 325.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux for 2-3 h until no further gas evolution
  3. customexcess thionyl chloride was removed under vacuum
  4. customThe crude intermediate was azeotroped with toluene (3×25 ml)
  5. customA dark brown solid was obtained
  6. filtrationThe solids were collected by filtration
  7. filtrationfiltered
  8. washwashed with hexane (50 ml)
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e3ecf307be0f46c29b8d605907d35510
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598247B2

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