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

HRID 578602

反応式

HRID 578602 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b82aa90264c945b48071577e904f9c19
出典データセット
uspto-grants-2015_05
特許番号
US09040174B2

関連ノート

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