Hydrazine hydrate (1:1) → 2-(3,5-Dichlorophenoxy)ethanamine hydrochloride (1:1)

HRID 637839Notes

Reaction equation

HRID 637839 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[O:5][CH2:6][CH2:7][N:8]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[O:5][CH2:6][CH2:7][NH2:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 7571580HCID 7571580, compound

Product 1

HCID 753664492-(3,5-Dichlorophenoxy)ethanamine hydrochloride (1:1)Yield 43.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 105.5 g (0.31 mole) of 2-[2-(3,5-dichlorophenoxy)ethyl]-1H-isoindole-1,3-(2H)-dione and 24.5 (0.41 mole) 85% hydrazine hydrate in 1 liter of 95% ethanol was heated at reflux for 4 hr. A white solid was filtered off and discarded. The filtrate was stripped to dryness and the residue partitioned between water and chloroform. The chloroform layer was washed with aqueous 10% sodium hydroxide solution and then extracted with 1N sulfuric acid. The aqueous acidic layer was made alkaline and extracted with chloroform. The chloroform layer was dried over magnesium sulfate and evaporated to obtain an oil, the free base of the title compound. A portion of the oil was reacted with ethereal hydrogen chloride to give white crystalline product in 43.2% yield, m.p. 229°-231° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hr
  3. filtrationA white solid was filtered off
  4. customthe residue partitioned between water and chloroform
  5. washThe chloroform layer was washed with aqueous 10% sodium hydroxide solution
  6. extractionextracted with 1N sulfuric acid
  7. extractionextracted with chloroform
  8. dry with materialThe chloroform layer was dried over magnesium sulfate
  9. customevaporated
  10. customto obtain an oil

Sources & evidence

ORD record
ord-ce16cfd24c8045db9253e62a8839baf5
Source dataset
uspto-grants-1985_12
Patent number
US04558155

Reaction notes

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