Diethyl[2-(4-nitrophenoxy)ethyl]amine → 4-(2-(Diethylamino)ethoxy)aniline

HRID 2415273Notes

Reaction equation

HRID 2415273 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:2]>C(O)C.[Pd]>[CH2:16]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:17]

Participants

4

Reactant 1

HCID 88294Diethyl[2-(4-nitrophenoxy)ethyl]amine

Product 1

HCID 4189324-(2-(Diethylamino)ethoxy)anilineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine (6.8 g, 28.3 mmol) (from Step A above) and 200 mg of 10% palladium-on-carbon in ethanol (150 mL) was hydrogenated at 20 psi in a Parr shaker for 1 hour. The mixture was filtered through Celite™ and the solvent was evaporated to give 5.36 g, (90%) 4-(2-diethylamino-ethoxy)-phenylamine.

Workup

  1. filtrationThe mixture was filtered through Celite™
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fd3fae7e77cd4d3f8fdc66ddd5d860f4
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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