N,N-Dimethyl-3-nitroaniline → N,N-dimethyl-m-phenylenediamine

HRID 2409437Notes

Reaction equation

HRID 2409437 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[CH:4]=1>CO.[Pd]>[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 69269N,N-Dimethyl-3-nitroaniline

Product 1

HCID 76084N,N-dimethyl-m-phenylenediamineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The compound (1.0 g, 6.08 mmol) prepared in step 1 was dissolved in methanol (25 ml) and added with 10%-palladium (Pd) (100 mg). The mixture was hydrogenated for 15 hours at room temperature under hydrogen gas. Once the reaction was completed, 10%-palladium (Pd) was removed by using celite-filter and the filtrate was concentrated to dryness. The residue was then purified by flash column chromatography (hexane:ethyl acetate=1:1) to obtain the title compound (700 mg, yield: 90%, colorless liquid).

Workup

  1. custom10%-palladium (Pd) was removed
  2. filtrationby using celite-filter
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residue was then purified by flash column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-9ad099c8fbe6418c9f56b6323c14b882
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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