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

HRID 266080

Reaction equation

HRID 266080 reaction equation
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

Participants

4

Reactant 2

HCID 2426774-(Benzoyloxy)cyclohexanoneHCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 218436753-Benzoyloxy-6-cyano-1,2,3,4-tetrahydrocarbazoleYield 47.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-d1372e2a424349d9a0e6770952a04bf1
Source dataset
uspto-grants-1997_07
Patent number
US05650426

Linked notes

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