Hydrochloric Acid → 2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid

HRID 566615Notes

Reaction equation

HRID 566615 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([OH:10])=[O:9])[CH2:3]1.[C:11]1([NH:17]N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(O)(=O)C.O>[CH2:3]1[C:2]2[NH:17][C:11]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:7]=2[CH2:6][CH2:5][CH:4]1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 27602523-Oxocyclohexane-1-carboxylic acid

Product 1

HCID 122920492,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acidYield 75.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 3-ketocyclohexanecarboxlic acid (4.78 g, 33.9 mmol) and phenyihydrazine (3.66 g, 40 mmol) in 35 mL of acetic acid was heated under reflux for one hour, then cooled, diluted with water and acidified with HCl. The resultant solid was collected by filtration, washed with water and dried to give 5.5 g of the title compound as a crystalline solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. temperaturecooled
  4. filtrationThe resultant solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-446b49fde81f4907968add2abcf9ec07
Source dataset
uspto-grants-2001_01
Patent number
US06175015B1

Reaction notes

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