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

HRID 1080045Notes

Reaction equation

HRID 1080045 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-db1de5bebcaf4e1390b7101cf2ba12cf
Source dataset
uspto-grants-1996_12
Patent number
US05580887

Reaction notes

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