Nitric Acid → 4,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 887619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887619
OS(O)(=O)=O.[CH3:6][C:7]1([CH3:17])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH2:9][CH2:8]1.[N+:18]([O-])([OH:20])=[O:19]>>[CH3:6][C:7]1([CH3:17])[C:16]2[C:11](=[CH:12][C:13]([N+:18]([O-:20])=[O:19])=[CH:14][CH:15]=2)[NH:10][CH2:9][CH2:8]1

Komponenten

4

Edukt 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 132194414,4-Dimethyl-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 219614774,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroquinoline

Versuchsvorschrift

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.

Aufarbeitung

  1. additionthe addition
  2. additionpoured into ice
  3. extractionextracted with EtOAc
  4. washThe organic portion was washed with brine, condensed
  5. custompurified by flash column chromatography (0 to 10% of EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ee96031364a24854932ec747576204c8
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247430B2

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