4-Nitrophenol → Diethyl[2-(4-nitrophenoxy)ethyl]amine

HRID 1584046Notes

Reaction equation

HRID 1584046 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17]Cl)[CH3:14]>CN(C=O)C>[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:14]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 13364Diethylaminoethyl chlorideHCID 24758Sodium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold solution of 41.8 g of 4-nitrophenol in 250 ml of DMF was added 16.0 g of a 57% dispersion of sodium hydride in mineral oil, followed by 46.0 g of 2-diethylaminoethyl chloride. After 20 hours, the mixture was filtered, freed of solvent by evaporation under reduced pressure, the residue dissolved in ether and washed with water. Extraction with 2N hydrochloric acid and basification of the extract gave N,N-diethyl-2-(4-nitrophenoxy)ethanamine.

Workup

  1. filtrationthe mixture was filtered
  2. customfreed of solvent by evaporation under reduced pressure
  3. dissolutionthe residue dissolved in ether
  4. washwashed with water
  5. extractionExtraction with 2N hydrochloric acid and basification of the extract

Sources & evidence

ORD record
ord-4b6956429f304d42ac987847760ea124
Source dataset
uspto-grants-1985_11
Patent number
US04555572

Reaction notes

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