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

HRID 2236693Notes

Reaction equation

HRID 2236693 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>C(O)C.Cl.[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

5

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 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N,N,N′-trimethyl-N′-(4-nitrophenyl)ethane-1,2-diamine in ethanol, containing 5 drops of concentrated hydrochloric acid, is hydrogenated overnight at atmospheric pressure over 10% Pd/C. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to give N-[2-(dimethylamino)ethyl]-N-methylbenzene-1,4-diamine as a dark maroon oil.

Workup

  1. filtrationThe mixture is filtered through a pad of diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d79220429324197adce225f9916ce86
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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