Reaktion #974801

Reaktionsgleichung

H2SO4

4,4-dimethyl-1,2,3,4-tetrahydro-quinoline

HNO3

H2SO4

→

titled compound

4,4-Dimethyl-7-nitro-1,2,3,4-tetrahydro-quinoline

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe addition
2. 2
   workup.ADDITIONpoured into ice
3. 3
   Extraktionextracted with EtOAc
4. 4
   WaschenThe organic portion was washed with brine, condensed
5. 5
   Sonstigepurified by flash column chromatography (0 to 10% of EtOAc in hexanes)

Vorschrift

To 13 ml of H2SO4 (96%) cooled in a salt ice bath was added dropwise 4,4-dimethyl-1,2,3,4-tetrahydro-quinoline (5.80 g, 36.0 mmol). The resulting slurry was stirred for 30 min, upon when concomitant addition of HNO3 (90%, 1.70 ml, 36.0 mmol) and H2SO4 (96%, 7 ml) was started, the addition was finished in 20 min, the mixture was stirred at 0° C. to 15° C. for 2 h, poured into ice, and extracted with EtOAc. The organic portion was washed with brine, condensed, and purified by flash column chromatography (0 to 10% of EtOAc in hexanes). The titled compound was obtained as a yellow oil. MS (ES+): 206.9 (M+H)+. Calc'd for C11H14N2O2—206.24.

Quelle