N,N-dimethyl-1-(3-methyl-4-nitrophenyl)methanamine → 4-[(Dimethylamino)methyl]-2-methylaniline
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
Product 1
Reagents, catalysts & solvents 2
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
- customPalladium on carbon was removed by filtration with Celite
- 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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