4-(Benzoyloxy)cyclohexanone → 3-Benzoyloxy-6-cyano-1,2,3,4-tetrahydrocarbazole

HRID 1683257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683257
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1)#[N:3].[C:12]([O:20][CH:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)(=O)C>[C:12]([O:20][CH:21]1[CH2:22][C:23]2[C:8]3[C:7](=[CH:6][CH:5]=[C:4]([C:2]#[N:3])[CH:9]=3)[NH:10][C:24]=2[CH2:25][CH2:26]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

4

Edukt 2

HCID 2426774-(Benzoyloxy)cyclohexanoneHCID 162129624-Cyanophenylhydrazine Hydrochloride

Produkt 1

HCID 218436753-Benzoyloxy-6-cyano-1,2,3,4-tetrahydrocarbazoleAusbeute 47,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

4-Cyanophenyl hydrazine hydrochloride (20.2 g) and 4-benzoyloxycyclohexanone (25.9 g) were dissolved in glacial acetic acid (400 ml) and the mixture was heated under reflux for 1.5 hr. After allowing to cool, the mixture was filtered, and the filtrate was evaporated to dryness, and neutralized with aqueous sodium bicarbonate solution to give a solid precipitate, which was purified by chromatography (SiO2 ; hexane/ethyl acetate) to give 3-benzoyloxy-6-cyano-1,2,3,4-tetrahydrocarbazole (18 g). This product (11.6 g) was suspended in ethanol (230 ml) and treated with 2.5% aqueous potassium hydroxide solution (120 ml), and heated under reflux for 1 hr. The cooled mixture was neutralized with glacial acetic acid and evaporated to a solid residue, which was washed with water, and dried to give 3-hydroxy-6-cyano-1,2,3,4-tetrahydrocarbazole (6.6 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. temperatureto cool
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. customto give a solid precipitate, which
  7. customwas purified by chromatography (SiO2 ; hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fc60db3753f7462f907d876e738d1245
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05637611

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