N-(3-Nitro-2,4-dimethyl-benzyl)-2,2-dimethyl-propionamide → N-(3-Amino-2,4-dimethyl-benzyl)-2,2-dimethyl-propionamide

HRID 410082Notes

Reaction equation

HRID 410082 reaction equation
[N+:1]([C:4]1[C:5]([CH3:19])=[C:6]([CH:15]=[CH:16][C:17]=1[CH3:18])[CH2:7][NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])([O-])=O>[Pd].CO>[NH2:1][C:4]1[C:5]([CH3:19])=[C:6]([CH:15]=[CH:16][C:17]=1[CH3:18])[CH2:7][NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 1

HCID 68032644N-(3-Nitro-2,4-dimethyl-benzyl)-2,2-dimethyl-propionamide

Product 1

HCID 56839979N-(3-Amino-2,4-dimethyl-benzyl)-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(3-nitro-2,4-dimethyl-benzyl)-2,2-dimethyl-propionamide (500 mg, 1.89 mmol), Pd/C (50 mg) and MeOH (20 mL) is stirred for 9 h under a hydrogen atmosphere (50 psi). The catalyst is removed by filtration and the filtrate is concentrated.

Workup

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

Sources & evidence

ORD record
ord-8cfc9b3c2343434c9e11ca27d24cf1f9
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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