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

HRID 1858185Notes

Reaction equation

HRID 1858185 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 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5 g (21 mmol) of 4-[2-(diethylamino)ethoxy]-nitrobenzene in 50 ml of ethanol was hydrogenated over 100 mg of 10% palladium-on-carbon at room temperature and under atmospheric pressure. After 4 hours the suspension was filtered through a filter aid and the filtrate was evaporated under reduced pressure to give 4 g (92%) of 4-[2-(diethylamino)ethoxy]-aniline as an oil.

Workup

  1. filtrationAfter 4 hours the suspension was filtered through a filter aid
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f458f73b1d0a4066aa07d194f605b34f
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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