Hydrazine hydrate (1:1) → cis-4-(3-Chlorophenyl)-but-3-enylamine

HRID 6720Notes

Reaction equation

HRID 6720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]\[CH2:10][CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[CH:6][CH:7]=1.O.NN>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]\[CH2:10][CH2:11][NH2:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58679826cis-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide

Product 1

HCID 58679830cis-4-(3-Chlorophenyl)-but-3-enylamineYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of cis-2-[4-(3-chlorophenyl)-but-3-enyl]-isoindole-1,3-dione (5.7 g) and hydrazine hydrate (1.8 mL) in ethanol (180 mL) was heated at reflux for 16 h. The solution was allowed to cool to rt and the volatiles were removed in vacuo. The resulting residue was dissolved in 2 M sodium hydroxide and extracted three times with ethyl acetate. The organic layers were combined, washed with brine, dried over magnesium sulfate and reduced in vacuo to yield cis-4-(3-chlorophenyl)-but-3-enylamine (2.5 g).

Workup

  1. temperatureat reflux for 16 h
  2. customthe volatiles were removed in vacuo
  3. dissolutionThe resulting residue was dissolved in 2 M sodium hydroxide
  4. extractionextracted three times with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-e071135198c14eb6b420a4e8a6fc2321
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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