Water → 4,5-Diazafluoren-9-one

HRID 1180683

Reaction equation

HRID 1180683 reaction equation
[N+](C1[CH:17]=[C:16]2[C:11]([N:12]=[CH:13][CH:14]=[CH:15]2)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-])=O.C([O-])(=O)C([O-])=[O:20].[K+].[K+].[OH-].[Na+].O>C(OCC)(=O)C>[N:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:17](=[O:20])[C:5]3[C:10](=[N:9][CH:8]=[CH:7][CH:6]=3)[C:11]=12

Participants

6

Reactant 4

HCID 962WaterHCID 11413Dipotassium OxalateHCID 14798Sodium HydroxideHCID 727905-Nitro-1,10-phenanthroline

Product 1

HCID 3421574,5-Diazafluoren-9-oneYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a 1 L one-necked flask was added a mixture of 30 g (0.13 mol, 68%) 5-nitro-1,10-phenanthroline, 51 g (0.61 mol) potassium oxalate, 12.5% NaOH(aq) 150 ml and 450 ml water. The mixture was then heated to reflux (100° C.) and stirred for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature. The reaction mixture was added with 1 L ethyl acetate, stirred for 30 minutes, and filtered to collect the filtrate. The residual solids were added into 300 ml ethyl acetate, stirred for 30 minutes and filtered to collect the filtrate. The combined filtrates were extracted to separate the organic layer, dehydrated by MgSO4, concentrated, and recrystallized from 200 ml methanol, so as to obtain light yellow solids cyclopenta[2,1-b;3,4-b′]dipyridin-5-one 13.3 g (0.07 mol, yield 54%).

Workup

  1. additionTo a 1 L one-necked flask was added
  2. temperatureThe mixture was then heated
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled to room temperature
  5. stirringstirred for 30 minutes
  6. filtrationfiltered
  7. customto collect the filtrate
  8. additionThe residual solids were added into 300 ml ethyl acetate
  9. stirringstirred for 30 minutes
  10. filtrationfiltered
  11. customto collect the filtrate
  12. extractionThe combined filtrates were extracted
  13. customto separate the organic layer
  14. concentrationconcentrated
  15. customrecrystallized from 200 ml methanol

Sources & evidence

ORD record
ord-67cec32dc96f459abfdccf7df882b11c
Source dataset
uspto-grants-2007_10
Patent number
US07282586B1

Linked notes

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