Hydrazine hydrate (1:1) → 2-(2-Chlorophenoxy)Ethylamine

HRID 1760925Notes

Reaction equation

HRID 1760925 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][N:7]1C(=O)C2=CC=CC=C2C1=O.O.NN>Cl>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][NH2:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27091102-[2-(2-chlorophenoxy)ethyl]isoindole-1,3-dione

Product 1

HCID 27357882-(2-Chlorophenoxy)Ethylamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

21.0 grams (0.071 ml) of N-[2-(2-chlorophenoxy)ethyl]phthalimide and 3.55 grams (0.071 mol) of hydrazine hydrate are dissolved in 70 ml of moisture-free alcohol for heating and diffusing over 45 minutes. And stirred with 20 ml 18% HCl heat for diffusing over 1.0 hour. Upon cooling, after filtrating the extracted solids, 20% NaOH is added to alkalize. The mixed solution's organic layer is extracted with chloroform and filtrating the extracted solids with potassium carbonate solution. The generated product is filled into silica gel columns utilizing the ratio of ethyl acetate as the diluent; upon purification, 2-(2-chlorophenoxy) ethylamine is obtained.

Workup

  1. temperaturefor heating
  2. temperatureheat
  3. waitfor diffusing over 1.0 hour
  4. temperatureUpon cooling
  5. filtrationafter filtrating the extracted solids, 20% NaOH
  6. additionis added
  7. extractionThe mixed solution's organic layer is extracted with chloroform
  8. filtrationfiltrating the extracted solids with potassium carbonate solution
  9. additionThe generated product is filled into silica gel columns
  10. customupon purification

Sources & evidence

ORD record
ord-e46dac1163774738b5e3b287f5c278be
Source dataset
uspto-grants-2005_01
Patent number
US06846826B2

Reaction notes

Loading…