Hydrochloric Acid → 3-(Ethylamino)-8-fluoro-1,2,3,4-tetrahydrocarbazole 3-Acetamido-8-fluoro-1,2,3,4-tetrahydrocarbazole

HRID 427169

Reaktionsgleichung

Reaktionsgleichung von HRID 427169
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].Cl.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20]N.Cl>C(O)C>[C:1]([NH:4][CH:5]1[CH2:10][C:9]2[C:16]3[C:15](=[C:14]([F:13])[CH:19]=[CH:18][CH:17]=3)[NH:20][C:8]=2[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[CH2:1]([NH:4][CH:5]1[CH2:10][C:9]2[C:16]3[C:15](=[C:14]([F:13])[CH:19]=[CH:18][CH:17]=3)[NH:20][C:8]=2[CH2:7][CH2:6]1)[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 538565N-(4-Oxocyclohexyl)acetamideHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)

Produkt 1

HCID 234702853-(Ethylamino)-8-fluoro-1,2,3,4-tetrahydrocarbazole 3-Acetamido-8-fluoro-1,2,3,4-tetrahydrocarbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A solution of 7.8 g. of 4-acetamidocyclohexanone and 8.1 g. of 2-fluorophenylhydrazine hydrochloride in 75 ml. of absolute ethyl alcohol and 25 ml. of 5-N hydrogen chloride in absolute ethyl alcohol was heated under reflux for two hours, cooled, filtered, and the filtrate was evaporated to dryness. The residue was dissolved in chloroform and adsorbed on a column of aluminum oxide. Dilution with ether yielded first a small amount of side-product followed by the desired product which was recrystallized by dissolving in methyl alcohol, adding toluene, and evaporation of the methyl alcohol, to give 10.5 g. of 3-acetamido-8-fluoro-1,2,3,4-tetrahydrocarbazole, m.p. 202°-204° C.

Aufarbeitung

  1. temperatureunder reflux for two hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness
  5. dissolutionThe residue was dissolved in chloroform
  6. customDilution with ether yielded first a small amount of side-product

Quellen und Nachweise

ORD-Eintrag
ord-d935b22c7ab44529aa7e7fea5d41d246
Quelldatensatz
uspto-grants-1979_10
Patentnummer
US04172834

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