Hydrochloric Acid → 2,3,4,9-tetrahydro-1H-carbazole-6-carboxylic acid

HRID 566613

Reaction equation

HRID 566613 reaction equation
[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)N.[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl>C(O)(=O)C.O>[CH2:14]1[C:13]2[NH:1][C:3]3[C:11](=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=3)[C:12]=2[CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 120894-Hydrazinobenzoic acid

Product 1

HCID 7298012,3,4,9-tetrahydro-1H-carbazole-6-carboxylic acidYield 50.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 4-hydrazinobenzoic acid (5.0 g, 32.9 mmol) and cyclohexanone (3.3 g, 33 mmol) in 30 mL of acetic acid was heated under reflux for 4 hours, then cooled, diluted with water and acidified with HCl. The resultant solid was collected by filtration, washed with water and dried to give 3.6 g of the title compound as a crystalline solid.

Workup

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

Sources & evidence

ORD record
ord-a336c49aa6f54100b388683c7a916533
Source dataset
uspto-grants-2001_01
Patent number
US06175015B1

Linked notes

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