3-Amino-N,N-dimethyl-4-nitroaniline → N4,N4-dimethylbenzene-1,2,4-triamine

HRID 1465802

Reaction equation

HRID 1465802 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-])=O)=[C:7]([CH:9]=1)[NH2:8]>[Pd].C(OCC)(=O)C.CO>[NH2:8][C:7]1[CH:9]=[C:3]([N:2]([CH3:13])[CH3:1])[CH:4]=[CH:5][C:6]=1[NH2:10]

Participants

4

Reactant 1

HCID 27334513-Amino-N,N-dimethyl-4-nitroaniline

Product 1

HCID 417238N4,N4-dimethylbenzene-1,2,4-triamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 5-dimethylamino-2-nitroaniline (1.94 g, 10.7 mmol) in 4:1 ethyl acetate/methanol (200 ml) was treated with 5% palladium on carbon (1.12 g) and stirred under an atmosphere of hydrogen at room temperature for 20.5 h. The suspension was quickly filtered through celite, the residue washed with methanol and the combined filtrate and washings concentrated to give the crude 2-amino-4-(dimethylamino)aniline as a dark brown oil, which was used without further purification in the next step.

Workup

  1. filtrationThe suspension was quickly filtered through celite
  2. washthe residue washed with methanol
  3. concentrationthe combined filtrate and washings concentrated

Sources & evidence

ORD record
ord-c3e59647387645ab94fce406eff33dbe
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Linked notes

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