Ammonium Chloride → 1-benzyl-3-iodo-1H-indazol-4-amine

HRID 79256Notes

Reaction equation

HRID 79256 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)[C:10]([I:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>C(O)C.O.C(OCC)(=O)C.[Fe]>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[C:10]([I:20])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 67259890HCID 67259890, compound

Product 1

HCID 672595921-benzyl-3-iodo-1H-indazol-4-amineYield 99.9%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

1-Benzyl-3-iodo-4-nitro-1H-indazole (340 mg; 0.897 mmol) was dissolved in a mixture of ethanol (8 mL) and water (2 mL). Ammonium chloride (24 mg; 0.45 mmol) and iron powder (501 mg; 8.97 mmol) were added and the mixture was stirred with heating to 75° C. under a nitrogen atmosphere for 4 hours. The mixture was allowed to cool, diluted with ethyl acetate (50 mL) and filtered through a pad of Celite. The solution was concentrated under reduced pressure to give 1-benzyl-3-iodo-1H-indazol-4-amine (313 mg) as a pale yellow oil.

Workup

  1. temperatureto cool
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-072e9b5204364a2989ef9a1231918e2c
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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