Glycerol → 7-Methyl-6-nitroquinoline

Reaktionsgleichung

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([CH3:14])[CH:6]=1)(=O)[CH3:2].O[CH2:16]C(CO)O.OS(O)(=O)=O>>[CH3:14][C:7]1[CH:6]=[C:5]2[C:10]([CH:16]=[CH:2][CH:1]=[N:4]2)=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12]

Komponenten

Edukt 3

HCID 753Glycerol

HCID 1118Sulfuric Acid

HCID 27373784-Acetamido-2-methylnitrobenzene

Produkt 1

HCID 36408347-Methyl-6-nitroquinolineAusbeute 34,4 %

Versuchsvorschrift

4-Acetamido-2-methylnitrobenzene (4.5 g; 23.2 mmol) glycerol (9 g; 100 mmol), H2SO4 conc (6.75 g) and As2O5.5H2O (3.6 g; 46.4 mmol) were heated at 130° C. for 20 h. The reaction mixture was poured on water, adjusted to pH 7-8 by adding NH3conc. and extracted with EtOAc three times. The combined organic phases were dried over Na2SO4, evaporated and purified via chromatography (SiO2; TBME/hexanes 70/30) to yield the title compound (1.5 g; 34%). The isomeric 5-methyl-6-nitroquinoline was eluted from the column after the title compound (850 mg; 19%).