Ammonium Chloride → 1-benzyl-1H-indazol-4-amine

HRID 706751Notes

Reaction equation

HRID 706751 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 213272561-benzyl-4-nitro-1H-indazole

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 1-benzyl-4-nitro-1H-indazole (150 mg; 0.592 mmol), iron powder (331 mg; 5.92 mmol) and ammonium chloride (16 mg; 0.296 mmol) in ethanol/water (4:1; 5 mL) was heated at reflux for 5 hours. The solvent was removed under vacuum and the residue was mixed with ethyl acetate/triethylamine (4:1; 5 mL) and heated at reflux for 1 hour. The mixture was allowed to cool and then filtered through a pad of silica, washing with ethyl acetate. The solvent was removed under vacuum to give the desired product that was used directly in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent was removed under vacuum
  4. additionthe residue was mixed with ethyl acetate/triethylamine (4:1; 5 mL)
  5. temperatureheated
  6. temperatureat reflux for 1 hour
  7. temperatureto cool
  8. filtrationfiltered through a pad of silica
  9. washwashing with ethyl acetate
  10. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-781ff00cfa7645309dd8757ccb2a0907
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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