Benzenamine, N,N,2-trimethyl-4-nitro- → 1-N,1-N,2-trimethylbenzene-1,4-diamine

HRID 450066Notes

Reaction equation

HRID 450066 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[CH3:12]>CO.[Pd]>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:1])[CH3:13])=[C:4]([CH3:12])[CH:5]=1

Participants

4

Reactant 1

HCID 141707Benzenamine, N,N,2-trimethyl-4-nitro-

Product 1

HCID 4363651-N,1-N,2-trimethylbenzene-1,4-diamineYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of dimethyl-(2-methyl-4-nitro-phenyl)-amine (0.49 g, 2.74 mmol) in methanol (10 ml) was hydrogenated over 10% Pd/C at 30 psi until no further gas uptake was observed. The reaction mixture was then filtered over celite and the filtrate evaporated to yield 4-amino-2-methyl-N,N-dimethyl aniline (0.3 g, 73%).

Workup

  1. filtrationThe reaction mixture was then filtered over celite
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-f27d90afe57948ab93ae79663c8203a4
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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