反応 #80441

反応方程式

4-Cyanophenyl hydrazine hydrochloride

4-benzoyloxycyclohexanone

→

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

収率 47.9%

溶媒

acetic acid

反応条件

後処理

1. 1
   温度the mixture was heated
2. 2
   温度under reflux for 1.5 hr
3. 3
   温度to cool
4. 4
   ろ過the mixture was filtered
5. 5
   その他the filtrate was evaporated to dryness
6. 6
   その他to give a solid precipitate, which
7. 7
   その他was purified by chromatography (SiO2 ; hexane/ethyl acetate)

実験手順

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).

出典