Ammonium Chloride → 4-(4-CHLORO-1H-PYRAZOL-1-YL)ANILINE

HRID 1709693Notes

Reaction equation

HRID 1709693 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[CH:6]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 23036556HCID 23036556, compound

Product 1

HCID 49130234-(4-CHLORO-1H-PYRAZOL-1-YL)ANILINE

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iron powder (0.75 g, 13.5 mmol) is added to a mixture of 4-chloro-1-(4-nitrophenyl)pyrazole (0.61 g, 2.7 mmol) and ammonium chloride (1.46 g, 27.0 mmol) in 45 ml ethanol and 16 ml water at 65°-70° over a period of 45 min. The reaction mixture is filtered and the solid is washed with ethyl acetate. Solvent is removed from the filtrate and the residue is taken into ethyl acetate, washed with water and with brine and dried to give 4-(4-chloro-1-pyrazolyl)aniline.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe solid is washed with ethyl acetate
  3. customSolvent is removed from the filtrate
  4. washwashed with water and with brine
  5. customdried

Sources & evidence

ORD record
ord-a9eeed514211485c8b19376254278c35
Source dataset
uspto-grants-1990_08
Patent number
US04950678

Reaction notes

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