Ethyl 4-(4-chloro-2-nitrobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate → ethyl 4-(4-chloro-2-aminobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate

HRID 1954746Notes

Reaction equation

HRID 1954746 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[C:9]([C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:10][NH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])=[C:4]([N+:28]([O-])=O)[CH:3]=1>B#[Ni]>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[C:9]([C:18](=[O:25])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:10][NH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])=[C:4]([NH2:28])[CH:3]=1

Participants

3

Reactant 1

HCID 18358884Ethyl 4-(4-chloro-2-nitrobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate

Product 1

HCID 18358872ethyl 4-(4-chloro-2-aminobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 82791nickel boride (NiB)Catalyst

Procedure

Following a procedure similar to that described in Example 23(d), ethyl 4-(4-chloro-2-nitrobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate (1.2g 2.81 mmol) was treated with nickel boride to afford crude product. The crude product was purified by flash chromatography eluting with hexanes:ethyl acetate (75:25-50:50) to give the title compound as a solid (620 mg, 56%).

Workup

  1. customto afford crude product
  2. customThe crude product was purified by flash chromatography
  3. washeluting with hexanes:ethyl acetate (75:25-50:50)

Sources & evidence

ORD record
ord-be3be3d95ed84d40a222567f9e2abbdd
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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