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

HRID 887619노트

반응식

HRID 887619 반응식
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

참가 물질

4

반응물 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2회HCID 132194414,4-Dimethyl-1,2,3,4-tetrahydroquinoline

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ee96031364a24854932ec747576204c8
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247430B2

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