Ammonium Chloride → 5-Amino4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole

HRID 1278879Notes

Reaction equation

HRID 1278879 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 222627595-Amino-1-(4-fluorophenyl)-4-(3-nitrobenzoyl)pyrazole

Product 1

HCID 222628105-Amino4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazoleYield 96.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-amino-1-(4-fluorophenyl)-4-(3-nitrobenzoyl)pyrazole (4.0 g, 24.52), Fe powder (3.84 g, 68 mmol) and ammonium chloride (3.84, 71.78 mmol) in ethanol (135 ml) and water (64 ml) was heated at reflux under nitrogen atmosphere. After 1 h, the reaction mixture was cooled to room temperature and stirred overnight. The reaction mixture was filtered through Celite® and the filtrate was concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The organic layer was separated and washed with brine, dried over sodium sulfate and concentrated in vacuo to give 5-amino-4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole (3.5 g) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen atmosphere
  3. filtrationThe reaction mixture was filtered through Celite®
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was partitioned between water and ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e93b07df772a41de9f346d82637b37b6
Source dataset
uspto-grants-2002_09
Patent number
US06444696B1

Reaction notes

Loading…