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

HRID 887619ノート

反応式

HRID 887619 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ee96031364a24854932ec747576204c8
出典データセット
uspto-grants-2012_08
特許番号
US08247430B2

反応ノート

読み込み中…