N,N-dimethyl-1-(3-methyl-4-nitrophenyl)methanamine → 4-[(Dimethylamino)methyl]-2-methylaniline

HRID 402671Notes

Reaction equation

HRID 402671 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([CH3:13])[CH:5]=1>C(O)C.[Pd]>[CH3:14][N:2]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([CH3:13])[CH:5]=1)[CH3:1]

Participants

4

Reactant 1

HCID 53486119N,N-dimethyl-1-(3-methyl-4-nitrophenyl)methanamine

Product 1

HCID 285994434-[(Dimethylamino)methyl]-2-methylanilineYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N,N-Dimethyl-1-(3-methyl-4-nitrophenyl)methanamine (0.80 g, 4.1 mmol) was dissolved in ethanol (5.0 mL) and 10% palladium on carbon (0.18 g) was added at ambient temperature. The reaction mixture was agitated under a hydrogen atmosphere at ambient temperature for 4 h. Palladium on carbon was removed by filtration with Celite and the solvent was removed under reduced pressure to afford 4-[(dimethylamino)methyl]-2-methylaniline (0.65 g, y. 96%).

Workup

  1. customPalladium on carbon was removed by filtration with Celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e677e9188b284e35ab5c00d4ae8ac866
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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