Bromine → HCID 135729099, compound

HRID 838982Notes

Reaction equation

HRID 838982 reaction equation
[Br:1]Br.[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[N:9][NH:10][C:11]2=[O:14])=[CH:6][CH:5]=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[OH-].[Na+]>[Br:1][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:4]=1[OH:3])[C:11](=[O:14])[NH:10][N:9]=[CH:8]2

Participants

5

Reactant 3

HCID 24408BromineHCID 656671Sodium PyrosulfiteHCID 135729098HCID 135729098, compound

Product 1

HCID 135729099HCID 135729099, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Bromine (20 g, 0.25 mole) was added to a stirred solution of 7-hydroxy-1(2H)phthalazinone (10g, 0.062 mole) in aqueous sodium hydroxide (2N, 140 ml), and the stirring was continued for two hours. An excess of sodium metabisulphite was added to the reaction mixture, and the precipitate was filtered off, washed with water and dried. This solid was suspended in acetic anhydride (17 ml) and was heated on a steam-bath for 30 minutes, and the solution was treated with charcoal, filtered and allowed to cool. The cooled mixture was filtered to give 7-acetoxy-6-bromophthalazone, which had m.p. 200°-201° after recrystallisation from ethanol. 7-Acetoxy-6-bromophthalazone was heated with 5% aqueous sodium hydroxide until a clear solution was obtained. The cooled solution was neutralised and the precipitate was filtered off to give 6-bromo-7-hydroxy-1(2H)-phthalazinone, m.p. > 320° (decomp.).

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with water
  3. customdried
  4. temperaturewas heated on a steam-bath for 30 minutes
  5. additionthe solution was treated with charcoal
  6. filtrationfiltered
  7. temperatureto cool
  8. filtrationThe cooled mixture was filtered
  9. customto give 7-acetoxy-6-bromophthalazone, which
  10. customafter recrystallisation from ethanol
  11. temperature7-Acetoxy-6-bromophthalazone was heated with 5% aqueous sodium hydroxide until a clear solution
  12. customwas obtained
  13. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-654d08f12ebb48fc8a50c6d5fb67595f
Source dataset
uspto-grants-1978_06
Patent number
US04093725

Reaction notes

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