Chlorosuccinimide → HCID 67974532, compound

HRID 706720Notes

Reaction equation

HRID 706720 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18]N1C(=O)CCC1=O>CN(C=O)C.O>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][C:13]([Cl:18])=[C:12]([NH2:17])[C:11]=2[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 213273171-benzyl-1H-indazol-4-amine

Product 1

HCID 67974532HCID 67974532, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-benzyl-1H-indazol-4-amine (0.080 g, 0.36 mmol) in DMF (2 mL) was treated with N-chlorosuccinimide (0.053 g, 0.39 mmol) at ambient temperature and stirred for 4 hours. The mixture was diluted with water, extracted with EtOAc, dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (10-50% EtOAc in hexanes) to provide 1-benzyl-5-chloro-1H-indazol-4-amine (0.035 g, 38% yield).

Workup

  1. extractionextracted with EtOAc
  2. customdried
  3. addition(phase separator silicone treated filter paper)
  4. concentrationconcentrated
  5. custompurified on silica gel (10-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c9a8d1fcf9e54a41817083bd900d3673
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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