Nitric Acid → 5-(4-Nitrophenyl)pyrazin-2(1H)-one

Reaktionsgleichung

[C:1]1([C:7]2[N:8]=[CH:9][C:10](=[O:13])[NH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[N+:19]([O-])([OH:21])=[O:20].N1C=CN=CC1=O>>[N+:19]([C:4]1[CH:3]=[CH:2][C:1]([C:7]2[N:8]=[CH:9][C:10](=[O:13])[NH:11][CH:12]=2)=[CH:6][CH:5]=1)([O-:21])=[O:20]

Komponenten

Edukt 4

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 727581,2-Dihydropyrazin-2-one

HCID 5990375-phenyl-1H-pyrazin-2-one

Produkt 1

HCID 138535735-(4-Nitrophenyl)pyrazin-2(1H)-one

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

5-Phenyl-2-(1H)-pyrazinone (56 g) was added in portions over 30 minutes to a stirred mixture of concentrated sulphuric acid (35 ml) and fuming nitric acid (200 ml). The temperature of the nitrating mixture was initially at -20° C. and care was taken to ensure that the temperature did not rise above -15° C. When the pyrazinone had completely dissolved the reaction mixture was allowed to warm to -10° C., stirred for a further 30 minutes, and poured slowly on to ice/water (1500 ml). A pale yellow solid precipitated which was collected by filtration, washed with a small amount of cold water and dried to afford 5-(4-nitrophenyl)-2-(1H)-pyrazinone (58.1 g).