Ethyl Alpha-oxo-3-(2-nitro-4,5-dichlorophenyl)propanoate → Ethyl 5,6-dichloro-1H-indole-2-carboxylate

HRID 1602997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1602997
O=[C:2]([CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([Cl:16])=[CH:11][C:10]=1[N+:17]([O-])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4]>CCO.C(O)(=O)C.[Fe]>[Cl:15][C:13]1[CH:14]=[C:9]2[C:10](=[CH:11][C:12]=1[Cl:16])[NH:17][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:8]2

Komponenten

5

Edukt 1

HCID 10733409Ethyl Alpha-oxo-3-(2-nitro-4,5-dichlorophenyl)propanoate

Produkt 1

HCID 10801165Ethyl 5,6-dichloro-1H-indole-2-carboxylateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl α-oxo-3-(2-nitro-4,5-dichlorophenyl)propanoate (100 g, 327 mmol) and iron powder (160 g) in EtOH (625 ml) and acetic acid (625 ml) was refluxed for two hours. After cooling, the resulting mixture was evaporated under vacuum and the solid residue was dissolved in THF (1000 ml) and chromatographed on Florisil (500 g) eluting with THF (5000 ml). Evaporation of the collected fractions gave pure title compound (77.5 g, 301 mmol, yield 92.0%) as a light brown powder, m.p. 215°-218° C.

Aufarbeitung

  1. temperaturewas refluxed for two hours
  2. temperatureAfter cooling
  3. customthe resulting mixture was evaporated under vacuum
  4. dissolutionthe solid residue was dissolved in THF (1000 ml)
  5. customchromatographed on Florisil (500 g)
  6. washeluting with THF (5000 ml)
  7. customEvaporation of the collected fractions

Quellen und Nachweise

ORD-Eintrag
ord-b2ebdb1b041b4143aa357d84939f00da
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05985905

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