3,5-Dimethyl-2-nitroaniline → (2-Amino-3,5-dimethylphenyl)amine

HRID 1610829Notes

Reaction equation

HRID 1610829 reaction equation
[CH3:1][C:2]1[C:3]([N+:10]([O-])=O)=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].[H][H]>C(O)C.[Pd]>[NH2:10][C:3]1[C:2]([CH3:1])=[CH:8][C:7]([CH3:9])=[CH:6][C:4]=1[NH2:5]

Participants

5

Reactant 2

HCID 222582263,5-Dimethyl-2-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 3613321(2-Amino-3,5-dimethylphenyl)amineYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2.50 g (15.0 mmol) of 3,5-Dimethyl-2-nitroaniline are dissolved in 50 ml ethanol. To this solution 250 mg (0.23 mmol) of palladium (10% on carbon) are added under argon. The mixture is treated for 24 h with hydrogen at ambient pressure and ambient temperature. The mixture is filtrated over celite and washed with ethanol. The solvent is evaporated under vacuum to yield 2.04 g (97.1% of th.) of 2-Amino-3,5-dimethylphenylamine.

Workup

  1. filtrationThe mixture is filtrated over celite
  2. washwashed with ethanol
  3. customThe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-c529910f73674cc68c9c2c6f2c2c033f
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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