HCID 13704246, Verbindung → HCID 59447961, Verbindung
Reaktionsgleichung
[C:1]([CH:3]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[N+:19]([O-])=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]>C(O)(=O)C.[Zn]>[NH2:2][C:1]1[NH:19][C:10]2[C:9]([C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:18][CH:17]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2Komponenten
4
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
In a 500 mL round-bottom flask were added methyl 4-(1-cyano-2-ethoxy-2-oxoethyl)-3-nitrobenzoate (14.9 g, 51.0 mmol) and zinc dust (16.7 g, 255 mmol) in acetic acid (255 mL) to give a gray suspension. The addition of zinc was done over 35 minutes at room temperature over an atmosphere of nitrogen and was fairly exothermic. The mixture was heated at 100° C. for 15 hours. The mixture was allowed to cool down, filtered through Celite and rinsed with ethyl acetate. Evaporation afforded a residue which was triturated in dichloromethane-hexanes and afforded, after filtration 6.3 g of the title compound. LCMS m/z 263.2 (M+H)+, retention time (on analytical HPLC)=1.90 minutes.