N-(4-chloro-3-fluoro-5-nitrobenzyl)-1-trifluoromethyl-cyclopropanecarboxamide → N-(3-Amino-4-chloro-5-fluoro-benzyl)-1-trifluoromethyl-cyclopropanecarboxamide

HRID 1258744Notes

Reaction equation

HRID 1258744 reaction equation
[Cl:1][C:2]1[C:18]([N+:19]([O-])=O)=[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[F:22]>[Ni].C1COCC1>[NH2:19][C:18]1[CH:17]=[C:5]([CH:4]=[C:3]([F:22])[C:2]=1[Cl:1])[CH2:6][NH:7][C:8]([C:10]1([C:13]([F:14])([F:15])[F:16])[CH2:11][CH2:12]1)=[O:9]

Participants

4

Reactant 1

HCID 67959823N-(4-chloro-3-fluoro-5-nitrobenzyl)-1-trifluoromethyl-cyclopropanecarboxamide

Product 1

HCID 67975171N-(3-Amino-4-chloro-5-fluoro-benzyl)-1-trifluoromethyl-cyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

H2 was passed through a shaken mixture of N-(4-chloro-3-fluoro-5-nitrobenzyl)-1-trifluoromethyl-cyclopropanecarboxamide (980 mg, 2.88 mmol), Ra—Ni (17 mg, 0.29 mmol) and THF (50 mL) at rt for 1.5 h. The mixture was filtered through celite and concentrated.

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-af6c8d8bf04e4102a44a172d28fcb01b
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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