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

HRID 898589Notes

Reaction equation

HRID 898589 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>CCO.[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-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5.770 g (25.842 mmol), N,N′-trimethyl-N′-(4-nitro-phenyl)-ethane-1,2-diamine (141a) and 0.60 g Pd/C (10%) in EtOH was hydrogenated for 4.5 h at 50 psi. The catalyst was filtered off and the filtrate evaporated down i. vac. The crude product was further reacted immediately.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated down i
  3. customThe crude product was further reacted immediately

Sources & evidence

ORD record
ord-7878492f0f3a4ecaa27b3ed7d9172791
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

Loading…