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

HRID 735034Notes

Reaction equation

HRID 735034 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH2:8][CH3:9])[CH2:6][CH3:7].[CH:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:12]([OH:19])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:6]([N:5]([CH2:8][CH3:9])[CH2:4][CH2:3][O:19][C:12]1[CH:11]=[CH:10][C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=1)[CH3:7]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

88.7 g (515.41 mmol) of (2-chloroethyl)diethylamine hydrochloride are added at ambient temperature to a suspension of 71.7 g (515.41 mmol) of p-nitrophenol and 284.94 g (2.061 mol) of potassium carbonate in 600 mL DMF and the reaction mixture is heated to 80° C. for 8 hours. The reaction mixture is evaporated down and the residue poured onto water and extracted with ethyl acetate. The organic phase is extracted three times with water and dried over sodium sulfate. The desiccant is filtered off and the filtrate is evaporated down. Yield: 110.52 g (90% of theory); C12H18N2O3 (M=238.28); Rf value: 0.52 (silica gel, dichloromethane/methanol (10:1)).

Workup

  1. customThe reaction mixture is evaporated down
  2. additionthe residue poured onto water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic phase is extracted three times with water
  5. dry with materialdried over sodium sulfate
  6. filtrationThe desiccant is filtered off
  7. customthe filtrate is evaporated down

Sources & evidence

ORD record
ord-417cbc1926b14571a1669de3308450dd
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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