Acetic Acid → 6-Chloro-1,2,3,4-tetrahydrocarbazole

HRID 542999

Reaktionsgleichung

Reaktionsgleichung von HRID 542999
C(O)(=O)C.C([O-])(=O)C.[Na+].[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([N+:24]([O-])=O)=[C:15]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2=O)[CH:16]=1>C(O)C.O.[Fe].C(O)(=O)C.[Fe]>[Cl:10][C:11]1[CH:16]=[C:15]2[C:14](=[CH:13][CH:12]=1)[NH:24][C:18]1[CH2:19][CH2:20][CH2:21][CH2:22][C:17]2=1

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 133483422-(5-Chloro-2-nitrophenyl)cyclo-hexanone

Produkt 1

HCID 3266156-Chloro-1,2,3,4-tetrahydrocarbazoleAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 45051903EisenazetatKatalysatorHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

The reduction can also be carried out using Fe/acetic acid. A mixture of 0.784 g of iron, 1.62 mL of glacial acetic acid, 0.544 g of sodium acetate, and 1 g of 2-(5-chloro-2-nitrophenyl)cyclo-hexanone was refluxed in 80 mL of 4:1 (v/v) ethanol/water for 2 hr. The mixture was cooled, ethanol was evaporated, and the residue was extracted into methylene chloride. Work-up followed by column chromatography on silica yielded 0.160 g (20%) of the named product.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customethanol was evaporated
  3. extractionthe residue was extracted into methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-aa4ae48d5d13481db8d30fcb815e7edd
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659862

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