Potassium Hydroxide → 4,5-Diazafluoren-9-one

HRID 1779132Notes

Reaction equation

HRID 1779132 reaction equation
O.[N:2]1[C:15]2[C:6](=C[CH:8]=[C:9]3[C:14]=2[N:13]=[CH:12][CH:11]=[CH:10]3)[CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[O-:18][Mn](=O)(=O)=O.[K+]>O>[CH:10]1[C:9]2[C:8](=[O:18])[C:6]3[C:15](=[N:2][CH:3]=[CH:4][CH:5]=3)[C:14]=2[N:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 212261,10-Phenanthroline hydrateHCID 516875Potassium Permanganate

Product 1

HCID 3421574,5-Diazafluoren-9-oneYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a boiling solution of phenanthroline monohydrate (2.2 g, 11.1 mol) and KOH (2 g, 35.5 mol) in water (130 ml), a hot solution of KMnO4 (5 g, 31.5 mol) in water (80 ml) was added dropwise over ca. 1 h. The mixture was refluxed for another 2 h, and then filtered hot. The orange filtrate was cooled and extracted with chloroform, the combined organic extracts were dried over anhydrous Na2SO4. After solvent removal, the crude product was further purified by column chromatography on silica gel using acetone/petroleum ether (2:1) as the eluent, the product was isolated as a yellow solid (980 mg, 48%). 1HNMR (ACETONE-D6,400 MHz): δ=8.80(d, J=5.0 Hz, 2H), 8.06 (d, J=7.5 Hz, 2H), 7.50 (dd, J1=7.5 Hz, J2=5.0 Hz, 2H). HRMS calcd for 182.1782, found 182.0369.

Workup

  1. temperatureThe mixture was refluxed for another 2 h
  2. filtrationfiltered hot
  3. temperatureThe orange filtrate was cooled
  4. extractionextracted with chloroform
  5. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  6. customAfter solvent removal
  7. customthe crude product was further purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8a1023c5a01e4cf9b238342957253482
Source dataset
uspto-grants-2016_02
Patent number
US09269908B2

Reaction notes

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