Реакция #81599

Уравнение реакции

4-Cyanophenyl hydrazine hydrochloride

4-benzoyloxycyclohexanone

→

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

Выход 47.9%

Растворители

acetic

Условия реакции

Обработка

1. 1
   Температураthe mixture was heated
2. 2
   Температураunder reflux for 1.5 hr
3. 3
   Температураto cool
4. 4
   Фильтрацияthe mixture was filtered
5. 5
   Другоеthe flitrate was evaporated to dryness
6. 6
   Другоеto give a solid precipitate, which
7. 7
   Другоеwas purified by chromatography (SiO2 ; hexane/ethyl acetate)

Методика

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).

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