Water → 1-Azaphenanthrene-5,6-dione

HRID 1640029Notes

Reaction equation

HRID 1640029 reaction equation
[N:1]1[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[O:15]=I(OI(=O)=O)=O.[OH2:22]>C(O)(=O)C>[N:1]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][C:8](=[O:22])[C:7]3=[O:15])[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6796Benzo(F)QuinolineHCID 159402Iodine pentoxide

Product 1

HCID 199224561-Azaphenanthrene-5,6-dioneYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
108 °C

Procedure

A solution of 68.3 g (381 mmol) of 1-azaphenanthrene and 157 g (470 mmol) of iodopentoxide in acetic acid was stirred under heat at 108° C. for 2 hours. After the reaction liquid had been cooled to room temperature, water was added to the reaction liquid to crystallize the product, and then the crystals were filtered off. Subsequently, the resultant crystal was dissolved in chloroform, washed with an aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium thiosulfate, dried, and exsiccated by concentration, whereby 53.9 g of 1-azaphenanthrene-5,6-dione were obtained (68% yield).

Workup

  1. customAfter the reaction liquid
  2. temperaturehad been cooled to room temperature
  3. customto crystallize the product
  4. filtrationthe crystals were filtered off
  5. dissolutionSubsequently, the resultant crystal was dissolved in chloroform
  6. washwashed with an aqueous solution of sodium hydrogen carbonate
  7. dry with materialan aqueous solution of sodium thiosulfate, dried
  8. concentrationexsiccated by concentration

Sources & evidence

ORD record
ord-89ca7b4e2bf44a12a69fb07c6f292caa
Source dataset
uspto-grants-2012_02
Patent number
US08110685B2

Reaction notes

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