N-(4-Chloro-3-nitrobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide → N-(3-amino-4-chlorobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

HRID 1258665Notes

Reaction equation

HRID 1258665 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[N+:19]([O-])=O>[Ni].CCOC(C)=O>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2([C:13]([F:15])([F:16])[F:14])[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[NH2:19]

Participants

4

Reactant 1

HCID 59529820N-(4-Chloro-3-nitrobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Product 1

HCID 59529866N-(3-amino-4-chlorobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(4-chloro-3-nitro-benzyl)-1-trifluoromethyl-cyclopropanecarboxamide (340 mg, 1.1 mmol), EtOAc (10 mL) and Ra—Ni (30 mg) was stirred at rt under a hydrogen atmosphere (3 bar). The catalyst was removed by filtration and the filtrate was concentrated to give the sub-title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-302a24cf37774c0e89455b41ef8cce08
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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