8-Methylquinoline → 8-Methyl-5-nitroquinoline

HRID 751060

반응식

HRID 751060 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[N+:12]([O-])([O-:14])=[O:13].[K+]>OS(O)(=O)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

참가 물질

4

반응물 2

HCID 119108-MethylquinolineHCID 24434Potassium Nitrate

생성물 1

HCID 2463008-Methyl-5-nitroquinoline수율 94%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

To a solution of commercially available 8-methylquinoline (5.0 g, 34 mmol) in concentrated H2SO4 (19 mL) at 0° C. was added portionwise KNO3 (4.29 g, 42.4 mmol). After the addition, the reaction was stirred at rt for 17 h, then poured into ice/water and extracted with EtOAc (3×100 mL). The aqueous layer was basified to pH=9 with solid Na2CO3 and extracted with EtOAc (2×100 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was chromatographed (silica gel) to yield the title compound (5.98 g, 94%) as a light yellow solid. LC/MS m/z 189 [M+H]+.

후처리

  1. additionAfter the addition
  2. extractionextracted with EtOAc (3×100 mL)
  3. extractionextracted with EtOAc (2×100 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed (silica gel)

출처 및 근거

ORD 기록
ord-7ca05091e8f4426e998fd20961bdae50
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405234B2

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