Hydrazine hydrate (1:1) → 3-(4-Trifluoromethylphenyl)-2-propenylamine

HRID 856055Notes

Reaction equation

HRID 856055 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][CH2:11]C23C=CC=CC2C(NC3=O)=O)=[CH:5][CH:4]=1.O.[NH2:26]N>C(O)C>[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][CH2:11][NH2:26])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 694807362-[3-(4-Trifluoromethylphenyl)-2-propenyl]phthalimide

Product 1

HCID 694813093-(4-Trifluoromethylphenyl)-2-propenylamineYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[3-(4-trifluoromethylphenyl)-2-propenyl]phthalimide (4.57 g, 13.79 mmol) prepared in Reference Example 102 and hydrazine hydrate (897 mg, 17.93 mmol) in ethanol (80 ml) was heated under reflux for 3 hours. The reaction mixture was allowed to return to room temperature and filtered, and the filtrate was concentrated under reduced pressure. To the residue, ethyl acetate was added, and the resulting mixture was washed with 1 N sodium hydroxide aqueous solution and brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to afford 3-(4-trifluoromethylphenyl)-2-propenylamine (2.78 g, quantitative) as a pale brown crystalline powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customto return to room temperature
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue, ethyl acetate was added
  7. washthe resulting mixture was washed with 1 N sodium hydroxide aqueous solution and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationAfter filtration
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-32f9446a45494c429fb93c407919d778
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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