Benzo(h)quinoline → 5H-Indeno(1,2-b)pyridin-5-one

HRID 578602

반응식

HRID 578602 반응식
[N:1]1[C:10]2[C:5](=C[CH:7]=[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]3=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[O-:17][Mn](=O)(=O)=O.[K+]>O>[N:1]1[CH:2]=[CH:3][CH:4]=[C:5]2[C:7](=[O:17])[C:8]3[C:9]([C:10]=12)=[CH:11][CH:12]=[CH:13][CH:14]=3

참가 물질

5

반응물 3

HCID 9191Benzo(h)quinolineHCID 14797Potassium HydroxideHCID 516875Potassium Permanganate

생성물 1

HCID 774895H-Indeno(1,2-b)pyridin-5-one수율 42%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A solution of benzo[h]quinoline (6 g, 33.5 mmol) and KOH (5.6 g, 100.5 mmol) in water (400 mL) was boiled. A hot solution of KMnO4 (14.8 g, 93.8 mmol) in water (240 mL) was added dropwise over 1 hour to the boiling solution. The mixture was refluxed for another 6 hours and filtered hot. The filtrate was allowed to cool to room temperature. The organic layer was extracted with chloroform and water, dried with anhydrous magnesium sulfate. After solvent removal, the residue was purified by column chromatography on silica (acetone-petroleum ether) to give product 2.5 g (42%) as a yellow solid.

후처리

  1. temperatureThe mixture was refluxed for another 6 hours
  2. filtrationfiltered hot
  3. extractionThe organic layer was extracted with chloroform and water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customAfter solvent removal
  6. customthe residue was purified by column chromatography on silica (acetone-petroleum ether)

출처 및 근거

ORD 기록
ord-b82aa90264c945b48071577e904f9c19
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040174B2

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