Ethanol → 6-Chloro-1,2,3,4-tetrahydrocarbazole

HRID 991998

Reaction equation

HRID 991998 reaction equation
[Cl:1][C:2]1C=C[C:5]([NH:8]N=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][CH:3]=1.[C:23]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.CC1C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(O)=O.[Na+].[CH2:47](O)[CH3:48]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:47][CH:48]=1)[NH:8][C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C:24]2=1

Participants

7

Reactant 5

HCID 702EthanolHCID 7967CyclohexanoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 9948495N-Benzhydrylidene-N'-(4-chlorophenyl)hydrazine

Product 1

HCID 3266156-Chloro-1,2,3,4-tetrahydrocarbazoleYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-(4-Chlorophenyl)benzophenone hydrazone (1.0 equiv., 0.5 mmol, 153 mg), cyclohexanone (1.5 equiv., 0.75 mmol, 0.078 mL), and TsOH.H2O (2 equiv., 1.0 mmol, 190 mg) were dissolved in ethanol (3 mL) and heated to reflux for 41 hours. The reaction mixture was then cooled to room temperature, diluted with Et2O (5 mL), neutralized with a saturated NaHCO3 solution, and extracted with Et2O (3×10 mL). The organic extracts were then dried over K2CO3, filtered and concentrated under vacuum. Purification by flash column chromatography (10% EtOAc/Hex) gave the title product as a white solid (94 mg, 0.46 mmol, 91% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 41 hours
  3. extractionextracted with Et2O (3×10 mL)
  4. dry with materialThe organic extracts were then dried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by flash column chromatography (10% EtOAc/Hex)

Sources & evidence

ORD record
ord-b5cc02631fb3440894aa78e21145b097
Source dataset
uspto-grants-2002_10
Patent number
US06465693B2

Linked notes

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