4-Nitrophenol → N,N-dimethyl-2-(4-nitrophenoxy)ethanamine

HRID 2109021Notes

Reaction equation

HRID 2109021 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.Cl.Cl[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:16][N:15]([CH2:14][CH2:13][O:10][C:3]1[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=1)[CH3:17]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 887421N,N-dimethyl-2-(4-nitrophenoxy)ethanamine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.2 g p-nitrophenol are dissolved in 200 ml acetone and 7.2 g 2-chloro-N,N-dimethylethylamin-hydrochloride and 11 g potassium carbonate are added. The mixture is stirred for 12 hours at reflux temperature. After cooling the salts are filtered off, the filtrate is evaporated down and the residue is taken up in methylene chloride. The organic phase is washed with water, dried over sodium sulphate and finally the solvent is eliminated.

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling the salts
  3. filtrationare filtered off
  4. customthe filtrate is evaporated down
  5. washThe organic phase is washed with water
  6. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-835f8eeaca044392be19a48fcc7cb830
Source dataset
uspto-grants-2009_04
Patent number
US07514468B2

Reaction notes

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