Pyridine → 8-Chloro-2,3,4,9-tetrahydro-1H-carbazole

HRID 597542Notes

Reaction equation

HRID 597542 reaction equation
[ClH:1].Cl[C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.N1C=CC=CC=1>O>[Cl:1][C:5]1[CH:4]=[CH:3][CH:8]=[C:7]2[C:6]=1[NH:9][C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7967CyclohexanoneHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

Product 1

HCID 144158218-Chloro-2,3,4,9-tetrahydro-1H-carbazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Chlorophenylhydrazine hydrochloride (1.79 g., 0.010 mole) is added to a solution of 1.0 ml. (0.010 mole ) cyclohexanone and 3.0 ml. pyridine. The resulting mixture is heated under nitrogen at reflux for 4 hours, cooled to room temperature and water added to precipitate the product. After crystallization from ethanol-water 1.34 g. of the title compound was obtained, M.P. 144.0°-145.5° C. A second crop of crystals 0.18 g. is obtained from the mother liquor. Total yield, 74%.

Workup

  1. temperatureThe resulting mixture is heated under nitrogen
  2. temperatureat reflux for 4 hours
  3. customto precipitate the product
  4. customAfter crystallization from ethanol-water 1.34 g

Sources & evidence

ORD record
ord-905645f4c1f94be38baea4a266769fb3
Source dataset
uspto-grants-1977_03
Patent number
US04014890

Reaction notes

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