4-Methoxy-2-phthalimido-3,5,6-trifluoro-1-nitrobenzene → 4-Methoxy-2-phthalimido-3,5,6-trifluoroaniline

HRID 358869Notes

Reaction equation

HRID 358869 reaction equation
[CH3:1][O:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[C:6]([N+:11]([O-])=O)=[C:5]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])[C:4]=1[F:25].[H][H]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[C:6]([NH2:11])=[C:5]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])[C:4]=1[F:25]

Participants

5

Reactant 2

HCID 200671344-Methoxy-2-phthalimido-3,5,6-trifluoro-1-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 200671534-Methoxy-2-phthalimido-3,5,6-trifluoroanilineYield 75.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1.3 g of 5% w/w palladium-on-carbon was added to a solution of 4.2 g (0.012 mole) of 4-methoxy-2-phthalimido-3,5,6-trifluoro-1-nitrobenzene (XXXIV) [prepared as described in Step (F1) above] in 150 ml of acetic acid, and the mixture was agitated vigorously for 1 hour in an atmosphere of hydrogen. At the end of this time, the reaction mixture was filtered, the filtrate was concentrated by evaporation under reduced pressure. and the solid which separated was washed with toluene, to afford 2.93 g of 4-methoxy-2-phthalimido-3,5,6-trifluoroaniline (XXXV) as colorless sandy crystals.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  3. customand the solid which separated
  4. washwas washed with toluene

Sources & evidence

ORD record
ord-d5ef09d8e118489fb4223b1d196eb440
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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