2-(2-Dimethylaminoethoxy)-4-nitroanisole → 3-(2-(Dimethylamino)ethoxy)-4-methoxyaniline

HRID 1419822Notes

Reaction equation

HRID 1419822 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[O:15][CH3:16]>C(O)C.[Pd]>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH:9]=[CH:8][C:7]=1[O:15][CH3:16])[NH2:12]

Participants

4

Reactant 1

HCID 107764242-(2-Dimethylaminoethoxy)-4-nitroanisole

Product 1

HCID 105603983-(2-(Dimethylamino)ethoxy)-4-methoxyanilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(2-dimethylaminoethoxy)-4-nitroanisole (D13, 11.8 g, 0.049 mole) in ethanol (200 ml) was hydrogenated over 10% Pd-C (1 g) at atmospheric temperature and pressure. The catalyst was filtered off through kieselguhr and the filtrate concentrated in vacuo to afford the title compound as a beige solid (10.3 g, 100%).

Workup

  1. filtrationThe catalyst was filtered off through kieselguhr
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-6d100e854ec349d3a004ea2ac4d23cef
Source dataset
uspto-grants-1999_03
Patent number
US05889022

Reaction notes

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