반응 #80441

반응 방정식

4-Cyanophenyl hydrazine hydrochloride

4-benzoyloxycyclohexanone

→

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

수율 47.9%

용매

acetic acid

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도under reflux for 1.5 hr
3. 3
   온도to cool
4. 4
   여과the mixture was filtered
5. 5
   기타the filtrate was evaporated to dryness
6. 6
   기타to give a solid precipitate, which
7. 7
   기타was purified by chromatography (SiO2 ; hexane/ethyl acetate)

실험 절차

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).

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