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

HRID 23920

Reaction equation

HRID 23920 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]>[Pd].C(O)C>[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 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(2-diethylaminoethoxy)-1-nitrobenzene (Method 10) (1.0 g, 4.2 mmol) and 10% palladium on charcoal catalyst (200 mg) in ethanol (30 ml) was stirred under an atmosphere of hydrogen for 3 hours. The catalyst was removed by filtration through diatomaceous earth and the filter pad was washed with methanol. The volatiles were removed from the filtrate by evaporation to give the title compound (400 mg, 46%) as an oil. M/z: 209 [MH]+.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. washthe filter pad was washed with methanol
  3. customThe volatiles were removed from the filtrate by evaporation

Sources & evidence

ORD record
ord-e9850bf8f4614397a428caf3690d3eee
Source dataset
uspto-grants-2005_02
Patent number
US06855719B1

Linked notes

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