Hydrazine hydrate (1:1) → 2,4,5-Trifluoro-3-methoxyaniline

HRID 358871Notes

Reaction equation

HRID 358871 reaction equation
O.NN.[CH3:4][O:5][C:6]1[C:7]([F:25])=[C:8]([N:14]2C(=O)C3=CC=CC=C3C2=O)[CH:9]=[C:10]([F:13])[C:11]=1[F:12]>C(O)C>[CH3:4][O:5][C:6]1[C:7]([F:25])=[C:8]([CH:9]=[C:10]([F:13])[C:11]=1[F:12])[NH2:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20067133N-(3-Methoxy-2,4,5-trifluorophenyl)-phthalimide

Product 1

HCID 27752772,4,5-Trifluoro-3-methoxyanilineYield 85.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.1 g (0.02 mole) of hydrazine hydrate was added to a suspension of 2.15 g (0.007 mole) of N-(3-methoxy-2,4,5-trifluorophenyl)phthalimide (XXXVI) [prepared as described in Step (F3) above] in 30 ml of ethanol, and the mixture was heated under reflux with stirring for 2 hours. The reaction mixture was cooled to room temperature and then filtered. The filtrate was concentrated by evaporation under reduced pressure, and the residue was dissolved in toluene. The resulting solution was washed with water and dried, and the solvent was then removed by evaporation under reduced pressure to afford 1.06 g of 3-methoxy-2,4,5-trifluoroaniline (XXIII) as pale brown needles.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  5. dissolutionthe residue was dissolved in toluene
  6. washThe resulting solution was washed with water
  7. customdried
  8. customthe solvent was then removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4e78f93e281f4646b98739d707826e81
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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