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

HRID 864113Notes

Reaction equation

HRID 864113 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, 40 mmol) 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 (73% of the desired compound, as a solid. The solid was recrystallized twice from toluene to afford 3.0 g of 3-(1-piperazinyl)-1H-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-34d4d352873a48baade96a67247d357f
Source dataset
uspto-grants-1996_10
Patent number
US05561128

Reaction notes

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