Pyridine → 1,2,3,4-Tetrahydrocarbazole

HRID 597541

Reaction equation

HRID 597541 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[C:9]1([NH:15]N)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1>O>[CH2:5]1[C:6]2[NH:15][C:9]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:1]=2[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7967CyclohexanoneHCID 60962Phenylhydrazine hydrochloride

Product 1

HCID 136641,2,3,4-Tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

Cyclohexanone (2.0 ml., 0.020 mole), phenylhydrazine hydrochloride (2.88 g., (0.020 mole) and 6.0 ml. of freshly distilled pyridine are combined, heated at reflux (115° C) for 3 hours, then allowed to cool to room temperature and allowed to stir overnight. About 25 ml. of water is added and the precipitated solids are collected by decantation. After washing again with water, the solids are dissolved in a mixture of 20 ml. of ethanol and 5 ml. of water and set aside. The resulting crystals are collected by filtration, washed with aqueous ethanol and dried to afford 2.65 g. (77.5% of theory) of the title compound, M.P. 119°-120° C. A mixture of the product and an authentic sample of 1,2,3,4-tetrahydrocarbazole also melted at 119°-120° C.

Workup

  1. temperatureheated
  2. temperatureto cool to room temperature
  3. customthe precipitated solids are collected by decantation
  4. washAfter washing again with water
  5. dissolutionthe solids are dissolved in a mixture of 20 ml
  6. filtrationThe resulting crystals are collected by filtration
  7. washwashed with aqueous ethanol
  8. customdried
  9. customto afford 2.65 g

Sources & evidence

ORD record
ord-d32beca789d94ffc8406731eb2d2faf5
Source dataset
uspto-grants-1977_03
Patent number
US04014890

Linked notes

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