N,N,N'-trimethyl-N'-(4-nitrophenyl)-1,2-ethanediamine → N-(2-Dimethylaminoethyl)-N-methylbenzene-1,4-diamine

HRID 1394181Notes

Reaction equation

HRID 1394181 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1>CO.[Pd]>[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 21873305N,N,N'-trimethyl-N'-(4-nitrophenyl)-1,2-ethanediamine

Product 1

HCID 21873395N-(2-Dimethylaminoethyl)-N-methylbenzene-1,4-diamineYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution containing 1.23 g of product from step 1 (5.5 mmol) in 20 mL MeOH, was added 0.6 g of Pd (5 wt. % on activated carbon). The resulting suspension was stirred under H2 (50 psi) at room temperature for 3 hours. The reaction mixture was filtered through celite. The filtrate was concentrated in vacuo to yield the title compound as a colorless oil (0.71 g, 67%). MS (ES+) m/e 194 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b00e55991f8e4913bd1971461ceaf661
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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