Sodium Hydroxide → HCID 178526490, compound

HRID 1269882Notes

Reaction equation

HRID 1269882 reaction equation
[Br:1]Br.[OH-].[Na+].[N+:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[CH:11]2)([O-:7])=[O:6].S([O-])(O)=O.[Na+]>O1CCOCC1>[Br:1][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=2)[NH:13][N:12]=1

Participants

6

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 215015-NitroindazoleHCID 24408BromineHCID 23665763Sodium Bisulfite

Product 1

HCID 178526490HCID 178526490, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of bromine (0.75 ml, 14.6 mmol) in a 2N-aqueous sodium hydroxide solution (20 ml) was added dropwise to a mixed solution of 5-nitro-1H-indazole (3.26 g, 20.0 mmol), dioxane (60 ml) and a 2N-aqueous sodium hydroxide solution (30 ml) at 0° C. and stirred at 0° C. for 30 minutes and then at room temperature for 3.5 hours. An aqueous sodium hydrogensulfite solution was added thereto until a solid was precipitated, to terminate the reaction, followed by extraction with ethyl acetate. The extract solution was washed with an aqueous sodium thiosulfate solution and a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was suspended in ethyl acetate and extracted with a 0.1N-aqueous sodium hydroxide solution. After 6 times of the extraction, the combined aqueous layer was acidified with hydrochloric acid and then re-extracted with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby 3-bromo-5-nitro-1H-indazole (0.93 g, 19%) was obtained.

Workup

  1. customuntil a solid was precipitated
  2. customto terminate
  3. customthe reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract solution was washed with an aqueous sodium thiosulfate solution
  6. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. extractionextracted with a 0.1N-aqueous sodium hydroxide solution
  10. extractionAfter 6 times of the extraction
  11. extractionre-extracted with ethyl acetate
  12. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  13. dry with materialdried over sodium sulfate
  14. distillationdistilled under reduced pressure
  15. customto remove the solvent

Sources & evidence

ORD record
ord-2ccd5072b99b41979492cef9793ee137
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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