Ammonium Chloride → HCID 39218501, compound

HRID 2110266Notes

Reaction equation

HRID 2110266 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[NH:10][N:9]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=2)[NH:10][N:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 57636437HCID 57636437, compound

Product 1

HCID 39218501HCID 39218501, compoundYield 28.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-(2-Chloro-phenyl)-6-nitro-1H-indazole (8.82 g, 32.23 mmol) was dissolved in 400 mL EtOH and 120 mL water, and the mixture was heated to 85° C. with stirring. After stirring for 40 minutes, Fe (9.0 g, 161.15 mmol) and NH4Cl (8.62 g, 161.15 mmol) were added, and the reaction mixture was stirred for 16 hours at 85° C. The reactuion mixture was filtered through Whatman filter paper, and the filtrate was concentrated under reduced pressure. The resulting residue was partitioned between water and ethyl acetate, and the organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed through silica gel (hexanes/EtOAc 0-50%) to give 2.24 g of 3-(2-Chloro-phenyl)-1H-indazol-6-ylamine, MS (M+H)=245.

Workup

  1. stirringAfter stirring for 40 minutes
  2. stirringthe reaction mixture was stirred for 16 hours at 85° C
  3. filtrationThe reactuion mixture was filtered through Whatman
  4. filtrationfilter paper
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was partitioned between water and ethyl acetate
  7. customthe organic layer was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was chromatographed through silica gel (hexanes/EtOAc 0-50%)

Sources & evidence

ORD record
ord-56e480a7850446dd93aae07a1e7c5fb3
Source dataset
uspto-grants-2009_04
Patent number
US07517901B2

Reaction notes

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