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

HRID 461549

Reaktionsgleichung

Reaktionsgleichung von HRID 461549
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

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1686d587e6dd4fe9b0e7dc2b9ed20cfd
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04062864

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