Ethyl 4-Cyano-2-nitrophenylacetate → 2-Oxindole-6-carbonitrile

HRID 1386341

Reaktionsgleichung

Reaktionsgleichung von HRID 1386341
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:7]=1[N+:14]([O-])=O)C>C(O)(=O)C.[Fe]>[C:12]([C:9]1[CH:8]=[C:7]2[C:6]([CH2:5][C:4](=[O:3])[NH:14]2)=[CH:11][CH:10]=1)#[N:13]

Komponenten

4

Edukt 1

HCID 21717235Ethyl 4-Cyano-2-nitrophenylacetate

Produkt 1

HCID 27733482-Oxindole-6-carbonitrileAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Iron powder (11.5 g, 205.2 mmol) was added to a saturated solution of ethyl(4-cyano-2-nitrophenyl)acetate (12 g, 51.3 mmol) in hot glacial acetic acid and the reaction mixture was stirred at 100° C. for 2 hours. The mixture was allowed to cool and poured into stirred ice water (1000 ml). The aqueous mixture was extracted with ethyl acetate, the extracts were combined, dried (MgSO4) and the solvent removed by evaporation. The solid residue was recrystallised from ethyl acetate to give 6-cyanooxindole (6.94 g, 85%).

Aufarbeitung

  1. temperatureto cool
  2. additionpoured
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation
  6. customThe solid residue was recrystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a8b936b9707b4e8d870f75c94a5c2f10
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265411B1

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