Ethenamine, N,N-dimethyl-2-nitro- → 4-Ethoxycarbonyl-3-(2-nitrovinyl)indole

HRID 569043

Reaktionsgleichung

Reaktionsgleichung von HRID 569043
[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)=[O:5])[CH3:2].CN([CH:18]=[CH:19][N+:20]([O-:22])=[O:21])C>C(OCC(F)(F)F)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH:18]=[CH:19][N+:20]([O-:22])=[O:21])=[CH:9][NH:10]2)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 518458Ethenamine, N,N-dimethyl-2-nitro-HCID 605034Ethyl indole-4-carboxylate

Produkt 1

HCID 540596304-Ethoxycarbonyl-3-(2-nitrovinyl)indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1362562,2,2-Trifluoroethyl AcetateLösungsmittel

Versuchsvorschrift

5 g of 4-ethoxycarbonyl indole are added to a solution of 3.1 g of dimethylamino-2-nitroethylene in 20 ml of trifluoroethyl acetate refrigerated under argon. The reaction mixture is introduced into ice water after it had been standing overnight at room temperature. The aqueous phase is repeatedly extracted with ethyl acetate. The combined ethyl acetate extracts are extracted first with sodium bicarbonate solution, then a saturated sodium chloride solution, dried and evaporated. The residue is recrystallized from ethanol. Yield: 4.5 g of 4-ethoxycarbonyl-3-(2-nitrovinyl)-indole. Yellow crystals with a 197°-199° C. melting point.

Aufarbeitung

  1. extractionThe aqueous phase is repeatedly extracted with ethyl acetate
  2. extractionThe combined ethyl acetate extracts are extracted first with sodium bicarbonate solution
  3. dry with materiala saturated sodium chloride solution, dried
  4. customevaporated
  5. customThe residue is recrystallized from ethanol
  6. customwith a 197°-199° C.

Quellen und Nachweise

ORD-Eintrag
ord-6f2a0ddab3ef4b25b66fd79945d51302
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04731358

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