Hydrochloric Acid → 9H-Cyclopenta[1,2-b:4,3-b']dipyridin-9-one

HRID 1463679Notes

Reaction equation

HRID 1463679 reaction equation
[CH:1]1[C:14]2[C:13]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:15])C(=O)[C:5]=2[N:4]=[CH:3][CH:2]=1.Cl>[OH-].[Na+]>[N:9]1[C:8]2[C:7](=[O:15])[C:5]3[C:14](=[CH:1][CH:2]=[CH:3][N:4]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 6764Phanquinone

Product 1

HCID 7259619H-Cyclopenta[1,2-b:4,3-b']dipyridin-9-oneYield 30.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 200 ml of 10% sodium hydroxide was added 10 g (47 mmole) of 4,7-phenanthrolin-5,6-quinone. This was heated in a water bath at 70°-80° with magnetic stirring for 2 hours. Then the reaction was cooled in an ice bath and acidified with concentrated hydrochloric acid to pH 4-5, keeping the mixture below 20°. The precipitate of side product, 5,6-dihydroxy-4,7-phenanthroline was filtered off and the filtrate was extracted with 5×50 ml of chloroform. After drying with sodium sulfate, the solvent was evaporated, yielding 2.6 g of 1,8-diazafluoren-9-one, m.p. 233°-234.5°.

Workup

  1. temperatureThis was heated in a water bath at 70°-80°
  2. temperatureThen the reaction was cooled in an ice bath
  3. customthe mixture below 20°
  4. filtrationThe precipitate of side product, 5,6-dihydroxy-4,7-phenanthroline was filtered off
  5. extractionthe filtrate was extracted with 5×50 ml of chloroform
  6. dry with materialAfter drying with sodium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-992ffc91895d4ca3913875ae146f317b
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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