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

HRID 706717Notes

Reaction equation

HRID 706717 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+]>[Fe].CCO.O>[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-amineYield 99%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of 1-benzyl-4-nitro-1H-indazole (0.404 g, 1.595 mmol), ammonium chloride (0.043 g, 0.798 mmol) in 4:1 v/v EtOH/water (10 mL) was treated with iron (0.891 g, 15.95 mmol) and refluxed for 2 hours. The mixture was concentrated and the residue taken in EtOAc/water, filtered through glass fiber filter paper and concentrated again to provide 1-benzyl-1H-indazol-4-amine (0.353 mg, 99% yield).

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe mixture was concentrated
  3. filtrationfiltered through glass fiber
  4. filtrationfilter paper
  5. concentrationconcentrated again

Sources & evidence

ORD record
ord-8cf920ee9d0b4aa597705a98737a8dd1
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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