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

HRID 887619Notes

Reaction equation

HRID 887619 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ee96031364a24854932ec747576204c8
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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