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

HRID 128108

Reaction equation

HRID 128108 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 six 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 filtration, 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 six 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. filtrationthe solids were collected by filtration
  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-5d665873a20349b0a6c95786c039b953
Source dataset
uspto-grants-1981_03
Patent number
US04257952

Linked notes

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