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

HRID 450076Notes

Reaction equation

HRID 450076 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>CO.[Pd]>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

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

Product 1

HCID 167782053-[2-(Dimethylamino)ethoxy]anilineYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of dimethyl-[2-(3-nitro-phenoxy)-ethyl]-amine (500 mg, 2.38 mmol) in methanol (20 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 concentrated to yield 3-(2-dimethylamino-ethoxy)-phenylamine (365 mg, 85%) as viscous oil.

Workup

  1. filtrationThe reaction mixture was then filtered over celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-41022280e2e74564b4abfb95f2a2d4d7
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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