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

HRID 379699

Reaction equation

HRID 379699 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)[CH2:4][CH3:5])[CH3:2]>[C].[Pd].CO>[CH2:1]([N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 1

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

Product 1

HCID 4189324-(2-(Diethylamino)ethoxy)anilineYield 98.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

N,N-diethyl-2-(4-nitrophenoxy)ethylamine (28.19 g) was dissolved into methanol (300 ml) and subjected to hydration reaction at ambient pressure by adding 10% palladium carbon catalyst (1.5 g). After completion of hydration reaction, catalyst was removed by filtration. Filtrate was concentrated under vacuum to obtain N,N-diethyl-2-(4-aminophenoxy)ethylamine (24.25 g) as color-less oily substance.

Workup

  1. customsubjected to hydration reaction at ambient pressure
  2. customAfter completion of hydration reaction, catalyst
  3. customwas removed by filtration
  4. concentrationFiltrate was concentrated under vacuum

Sources & evidence

ORD record
ord-72a8bec4006c486aac01b693cc55603e
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Linked notes

Loading…