Sodium Carbonate → 4-Keto-9-methylphenazine

HRID 64771Notes

Reaction equation

HRID 64771 reaction equation
[CH3:1][O:2]S([O-])(=O)=O.[CH3:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:21]=1[N:20]=[C:19]1[C:14](C=[CH:16][CH:17]=[CH:18]1)=[NH+:13]2.C(=O)([O-])[O-].[Na+].[Na+]>O>[O:2]=[C:1]1[C:14]2[C:19](=[N:20][C:21]3[C:12]([N:13]=2)=[CH:11][CH:10]=[CH:9][C:8]=3[CH3:7])[CH:18]=[CH:17][CH2:16]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 178503009HCID 178503009, compound

Product 1

HCID 704526314-Keto-9-methylphenazineYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g (0.011 mol) of 9-methylphenazinium methylsulphate are dissolved in 2 l of distilled water and then exposed for 24 hours to UV-radiation (from a source having a power 1.5 kW, at a distance of 30-40 cm) at the temperature of 40° C. in a closed quartz flask, then added with a 0.1M solution of sodium carbonate to the pH of 9.0. Then the irradiation is continued for additional 4 hours. The solution is filtered, added with 40 ml of a 10% solution of sodium carbonate and extracted four times with 200 ml portions of chloroform. The extracts are combined, dried with potassium carbonate and evaporated to the volume of 70 ml, then 250 ml of hot hexane are added and the mixture is cooled. The formed precipitate is filtered off, washed with 200 ml of hexane, recrystallized from 50 ml of water to give 0.83 g of 4-keto-9-methylphenazine (61%) in the form of blue crystals melting at 133°-135° C.

Workup

  1. customThen the irradiation
  2. waitis continued for additional 4 hours
  3. filtrationThe solution is filtered
  4. additionadded with 40 ml of a 10% solution of sodium carbonate
  5. extractionextracted four times with 200 ml portions of chloroform
  6. dry with materialdried with potassium carbonate
  7. customevaporated to the volume of 70 ml
  8. addition250 ml of hot hexane are added
  9. temperaturethe mixture is cooled
  10. filtrationThe formed precipitate is filtered off
  11. washwashed with 200 ml of hexane
  12. customrecrystallized from 50 ml of water

Sources & evidence

ORD record
ord-225a68c5bbc243ed8a609062a5d8dc81
Source dataset
uspto-grants-1986_09
Patent number
US04610767

Reaction notes

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