Sodium Hydroxide → 3-(Piperazin-1-YL)-1H-indazole

HRID 2248578Notes

Reaction equation

HRID 2248578 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([N:10]2[CH2:15][CH2:14][N:13](C#N)[CH2:12][CH2:11]2)=[N:2]1.[OH-].[Na+]>OS(O)(=O)=O>[N:10]1([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14823453HCID 14823453, compound

Product 1

HCID 148234453-(Piperazin-1-YL)-1H-indazoleYield 73%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 4-(1H-indazol-3-yl)-1-piperazinecarbonitrile (8.0 g), and 25% H2SO4 (100 ml) was stirred at reflux for 4.5 hours. The reaction was cooled in an ice bath and made basic by the dropwise addition of 50% NaOH. The basic solution was extracted with ethyl acetate. The ethyl acetate was washed with H2O, dried with MgSO4 and concentrated to afford 5.2 g of the desired compound, as a solid. The sample was recrystallized twice from toluene to afford 3.0 g of the unsubstituted indazole, m.p. 153°-155° C.

Workup

  1. temperatureat reflux for 4.5 hours
  2. temperatureThe reaction was cooled in an ice bath
  3. extractionThe basic solution was extracted with ethyl acetate
  4. washThe ethyl acetate was washed with H2O
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-353116233d2e4dc5827a34b831e0efdf
Source dataset
uspto-grants-1991_08
Patent number
US05041445

Reaction notes

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