Acetic Acid → 4-Oxo-1,2,3,4-tetrahydro-7H-benzo[c]carbazole-8-carboxylic acid

HRID 617806

Reaktionsgleichung

Reaktionsgleichung von HRID 617806
Cl.[NH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])N.[C:13]([OH:16])(=O)[CH3:14].Cl[C:18]1[C:19](=O)[C:20]([C:28]#N)=[C:21]([C:26]#N)[C:22](=O)[C:23]=1Cl>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[O:16]=[C:13]1[C:14]2[CH:28]=[CH:20][C:19]3[NH:2][C:4]4[C:12]([C:18]=3[C:23]=2[CH2:22][CH2:21][CH2:26]1)=[CH:11][CH:10]=[CH:9][C:5]=4[C:6]([OH:8])=[O:7]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)

Produkt 1

HCID 218499384-Oxo-1,2,3,4-tetrahydro-7H-benzo[c]carbazole-8-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

5.4 g (28.6 mmol) of 2-hydrazinobenzoic acid hydrochloride and 4.7 g (34.3 mmol) of zinc chloride were added to 300 ml of glacial acetic acid. Under stirring at about 85° C., 4.7 g (28.6 mmol) of the compound of Production Example 6 was added thereto over about 5 minutes. Then the obtained mixture was stirred at the same temperature for about 2 hours, brought back to room temperature and the precipitate was recovered by filtration. After concentrating the filtrate, water was added thereto and the precipitate thus formed was recovered by filtration. These precipitates were combined, dried and then dissolved in about 500 ml of dimethylformamide. Under stirring at room temperature, a solution of 6.5 g (28.6 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in tetrahydrofuran (20 ml) was added thereto and the obtained mixture was stirred for about 30 minutes. After concentrating, about 50 ml of ethanol was added and the precipitate thus formed was recovered by filtration to thereby give 3.4 g of the title compound.

Aufarbeitung

  1. stirringThen the obtained mixture was stirred at the same temperature for about 2 hours
  2. custombrought back to room temperature
  3. filtrationthe precipitate was recovered by filtration
  4. concentrationAfter concentrating the filtrate, water
  5. additionwas added
  6. customthe precipitate thus formed
  7. filtrationwas recovered by filtration
  8. customdried
  9. dissolutiondissolved in about 500 ml of dimethylformamide
  10. stirringUnder stirring at room temperature
  11. stirringthe obtained mixture was stirred for about 30 minutes
  12. concentrationAfter concentrating
  13. additionabout 50 ml of ethanol was added
  14. customthe precipitate thus formed
  15. filtrationwas recovered by filtration

Quellen und Nachweise

ORD-Eintrag
ord-8b4671ea111a4c02b29bb02f96d9af51
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952335

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