Réaction #81599

Équation de réaction

4-Cyanophenyl hydrazine hydrochloride

4-benzoyloxycyclohexanone

→

3-benzoyloxy-6-cyano-1,2,3,4-tetrahydrocarbazole

Rendement 47.9%

Solvants

acetic

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was heated
2. 2
   Températureunder reflux for 1.5 hr
3. 3
   Températureto cool
4. 4
   Filtrationthe mixture was filtered
5. 5
   Autrethe flitrate was evaporated to dryness
6. 6
   Autreto give a solid precipitate, which
7. 7
   Autrewas purified by chromatography (SiO2 ; hexane/ethyl acetate)

Mode opératoire

4-Cyanophenyl hydrazine hydrochloride (20.2 g) and 4-benzoyloxycyclohexanone (25.9 g) were dissolved in glacial acetic (400 ml) and the mixture was heated under reflux for 1.5 hr. After allowing to cool, the mixture was filtered, and the flitrate 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).

Source