Sodium Hydroxide → 4-(2-(Diethylamino)ethoxy)aniline

HRID 1164971Notes

Reaction equation

HRID 1164971 reaction equation
Br.[CH2:2]([N:4]([CH2:19][CH3:20])[CH2:5][CH2:6][O:7][C:8]1[C:13](C)=[CH:12][C:11]([N+:15]([O-])=O)=[CH:10][C:9]=1C)[CH3:3].O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[CH2:19]([N:4]([CH2:2][CH3:3])[CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:15])=[CH:12][CH:13]=1)[CH3:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 19863395HCID 19863395, compound

Product 1

HCID 4189324-(2-(Diethylamino)ethoxy)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 8.0 g (23 mmol) of N,N-diethyl-2-(2,6-dimethyl-4-nitrophenoxy)ethanamine hydrobromide in 90 mL of ethanol add 26.0 g (115 mmol) of tin(II) chloride dihydrate. Heat the mixture to reflux with stirring for 1.5 h. Cool the mixture and pour it onto ice-water. Adjust the pH to 12 by the addition of dilute sodium hydroxide. Add ethyl acetate and filter the mixture through celite. Extract the filtrate twice with ethyl acetate. Wash the extract with saturated sodium chloride solution and dry over anhydrous sodium sulfate. Remove the drying agent by filtration and emove the solvent in vacuo to yield the title compound.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. temperatureCool the mixture
  4. additionpour it onto ice-water
  5. filtrationAdd ethyl acetate and filter the mixture through celite
  6. extractionExtract the filtrate twice with ethyl acetate
  7. washWash the
  8. extractionextract with saturated sodium chloride solution
  9. dry with materialdry over anhydrous sodium sulfate
  10. customRemove the drying agent
  11. filtrationby filtration

Sources & evidence

ORD record
ord-8323f3bcfa93453ea9a37749bb6bfaf3
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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