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

HRID 578602

Reaction equation

HRID 578602 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b82aa90264c945b48071577e904f9c19
Source dataset
uspto-grants-2015_05
Patent number
US09040174B2

Linked notes

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