1,10-Phenanthroline-5,6-dione → 1,10-Phenanthroline-5,6-diol

HRID 18901

Reaction equation

HRID 18901 reaction equation
[N:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][N:12]=3)[C:7](=[O:15])[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.S1C=C[CH-]OS1>C(O)C>[OH:15][C:7]1[C:6]([OH:16])=[C:5]2[C:14]([N:1]=[CH:2][CH:3]=[CH:4]2)=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2

Participants

4

Reactant 2

HCID 728101,10-Phenanthroline-5,6-dioneHCID 178420855CID 86608576

Product 1

HCID 1355145541,10-Phenanthroline-5,6-diolYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g of 1,10-phenanthroline-5,6-dione (reagent; manufactured and sold by Sigma-Aldrich Co., U.S.A.) and 0.691 g of dithioxamide (reagent; manufactured and sold by Tokyo Kasei Kogyo Co., Ltd., Japan) were added to 40 ml of ethanol, and the resultant mixture was refluxed under heating in an atmosphere of air for 13 hours. The resultant reaction mixture was allowed to cool to room temperature, and subjected to a suction filtration using a filter paper (pore diameter: 1 μm), thereby obtaining powders. For removing substances remaining unreacted in the obtained powders, the powders were washed with 100 ml of chloroform at room temperature while stirring, followed by a suction filtration using a filter paper (pore diameter: 1 μm), thereby obtaining 0.759 g of 5,6-dihydroxy-1,10-phenanthroline in the form of powders.

Workup

  1. temperatureunder heating in an atmosphere of air for 13 hours
  2. customThe resultant reaction mixture
  3. filtrationsubjected to a suction filtration
  4. customobtaining powders
  5. customFor removing substances
  6. washthe powders were washed with 100 ml of chloroform at room temperature
  7. filtrationfollowed by a suction filtration

Sources & evidence

ORD record
ord-80090cb4b96f438383d80b63241d889f
Source dataset
uspto-grants-2010_06
Patent number
US07741559B2

Linked notes

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