Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1) → 3-(Dimethylamino)-8-carboxy-1,2,3,4-tetrahydrocarbazole

HRID 1077351Notes

Reaction equation

HRID 1077351 reaction equation
CN(C)C1CCC(=O)CC1.Cl.C(C1C=CC=CC=1NN)(O)=O.O.[CH3:24][N:25]([CH3:42])[CH:26]1[CH2:38][C:37]2[C:36]3[C:31](=[C:32]([C:39]([OH:41])=[O:40])[CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]=2[CH2:28][CH2:27]1>C(O)C>[CH3:24][N:25]([CH3:42])[CH:26]1[CH2:38][C:37]2[C:36]3[C:31](=[C:32]([C:39]([OH:41])=[O:40])[CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]=2[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)HCID 103745454-(Dimethylamino)cyclohexan-1-oneHCID 234703133-(Dimethylamino)-8-carboxy-1,2,3,4-tetrahydrocarbazole hydrate

Product 1

HCID 128918623-(Dimethylamino)-8-carboxy-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 14.1 g. of 4-dimethylaminocyclohexanone and 18.9 g. of 2-carboxyphenylhydrazine hydrochloride in 150 ml. of absolute ethyl alcohol was heated under reflux for 6 hours, cooled, and the resulting crystalline 4-dimethylaminocyclohexanone 2-carboxyphenylhydrazone hydrochloride was collected by filtration, washed with isopropyl alcohol and ether, suspended in 200 ml. of 2% hydrogen chloride in acetic acid and heated at reflux for eight hours. The mixture was cooled and the solids were collected by filtraton, washed with isopropyl alcohol and dissolved in 400 ml. of water. The aqueous solution was treated with alkali until neutral and allowed to stand for two hours. The resulting crystals were filtered to give, on recrystallization from water, 30.3 g. of 3-(dimethylamino)-8-carboxy-1,2,3,4-tetrahydrocarbazole hydrate, m.p. > 300°C. (dec.)

Workup

  1. temperatureunder reflux for 6 hours
  2. temperaturecooled
  3. filtrationthe resulting crystalline 4-dimethylaminocyclohexanone 2-carboxyphenylhydrazone hydrochloride was collected by filtration
  4. washwashed with isopropyl alcohol and ether
  5. temperatureof 2% hydrogen chloride in acetic acid and heated
  6. temperatureat reflux for eight hours
  7. temperatureThe mixture was cooled
  8. customthe solids were collected by filtraton
  9. washwashed with isopropyl alcohol
  10. dissolutiondissolved in 400 ml
  11. additionThe aqueous solution was treated with alkali until neutral and
  12. filtrationThe resulting crystals were filtered
  13. customto give, on recrystallization from water, 30.3 g

Sources & evidence

ORD record
ord-1d213b3382cf4666939e97fa4b8b86c8
Source dataset
uspto-grants-1976_05
Patent number
US03959309

Reaction notes

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