N-(4-Chloro-3-nitrobenzyl)-2,2-dimethyl-propionamide → N-(3-amino-4-chlorobenzyl)pivalamide

HRID 1258633Notes

Reaction equation

HRID 1258633 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][C:3]=1[N+:16]([O-])=O>[Ni].C1COCC1>[NH2:16][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:2]=1[Cl:1])[CH2:6][NH:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 1

HCID 66765017N-(4-Chloro-3-nitrobenzyl)-2,2-dimethyl-propionamide

Product 1

HCID 66765386N-(3-amino-4-chlorobenzyl)pivalamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(4-chloro-3-nitrobenzyl)-2,2-dimethyl-propionamide (5.92 g, 21.9 mmol), THF (150 mL) and Ra—Ni (1.50 g) was stirred for 2 days at RT under a hydrogen atmosphere (3.0 bar). The catalyst was removed by filtration and the mixture was concentrated. The crude was purified by chromatography to give the sub-title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe mixture was concentrated
  3. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-42ea93736e544431ae00ed7ce6f6eeca
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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