6-Nitro-2,4-xylidine → (2-Amino-3,5-dimethylphenyl)amine

HRID 2105005Notes

Reaction equation

HRID 2105005 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([N+:10]([O-])=O)[CH:3]=1>CO.[Pd]>[CH3:9][C:7]1[CH:8]=[C:2]([CH3:1])[CH:3]=[C:4]([NH2:10])[C:5]=1[NH2:6]

Participants

4

Reactant 1

HCID 742196-Nitro-2,4-xylidine

Product 1

HCID 3613321(2-Amino-3,5-dimethylphenyl)amineYield 109.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4,6-dimethyl-2-nitroaniline (312 mg) in 5 mL MeOH, was added 10% Pd/C (50 mg). The mixture evacuated and flushed with H2 (3×), then was stirred under an atmosphere of H2 for 6 h. Conc. HCl (2 drops) was added and the mixture was stirred under H2 for an additional 18 h, then was filtered and concentrated to afford 280 mg of Intermediate 179.1, which was used without further purification.

Workup

  1. customThe mixture evacuated
  2. customflushed with H2 (3×)
  3. additionConc. HCl (2 drops) was added
  4. stirringthe mixture was stirred under H2 for an additional 18 h
  5. filtrationwas filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1bc3b5547da04e498502849c965ca773
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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