1-(2-Dimethylaminoethoxy)-3-nitrobenzene → 3-[2-(Dimethylamino)ethoxy]aniline

HRID 1740792Notes

Reaction equation

HRID 1740792 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1>C(O)C.[Pd]>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[NH2:12]

Participants

4

Reactant 1

HCID 218331171-(2-Dimethylaminoethoxy)-3-nitrobenzene

Product 1

HCID 167782053-[2-(Dimethylamino)ethoxy]anilineYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(2-dimethylaminoethoxy)-3-nitrobenzene (4.64 g, 22 mmol) in ethanol (200 ml) was added 10% palladium catalyst on charcoal (1 g). The reaction mixture was hydrogenated at atmospheric pressure for 2 hours, then filtered through kieselguhr and evaporated under reduced pressure to give the product as a yellow oil (4.0 g, 100%).

Workup

  1. filtrationfiltered through kieselguhr
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3e70545810ac4c49ab35e03deb1241ad
Source dataset
uspto-grants-1999_10
Patent number
US05972937

Reaction notes

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