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

HRID 706766Notes

Reaction equation

HRID 706766 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.[NH4+].[Cl-]>CCO.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-amineYield 61.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

1-Benzyl-4-nitro-1H-indazole (672 mg, 2.65 mmol) was taken up in 26 mL of EtOH/water (4:1) and treated with NH4Cl (0.5 equivalents) and Fe powder (10 equivalents). The reaction was heated to reflux for 2 hours. The reaction was concentrated under reduced pressure, diluted with EtOAc:Et3N (4:1) and stirred for two hours. The reaction mixture was filtered over GF/F paper and concentrated to give a brown, viscous oil. This crude material was purified by column chromatography (30% EtOAc/hexanes) providing 363 mg (61%) of the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction was concentrated under reduced pressure
  4. additiondiluted with EtOAc:Et3N (4:1)
  5. filtrationThe reaction mixture was filtered over GF/F paper
  6. concentrationconcentrated
  7. customto give a brown, viscous oil
  8. customThis crude material was purified by column chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8191ee566e7344eaa0bd5b41795ca8c7
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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