2-(4-Nitro-3-pentafluorosulfanylphenyl)isoindole-1,3-dione → 2-(4-Amino-3-pentafluorosulfanylphenyl)isoindole-1,3-dione

HRID 2356661Notes

Reaction equation

HRID 2356661 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:6][C:5]=1[S:21]([F:26])([F:25])([F:24])([F:23])[F:22])([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:6][C:5]=1[S:21]([F:26])([F:25])([F:22])([F:23])[F:24]

Participants

5

Reactant 2

HCID 596421452-(4-Nitro-3-pentafluorosulfanylphenyl)isoindole-1,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 596421372-(4-Amino-3-pentafluorosulfanylphenyl)isoindole-1,3-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.94 g (4.92 mmol) of 2-(4-nitro-3-pentafluorosulfanylphenyl)isoindole-1,3-dione 51.5 were dissolved in 20 ml of methanol, admixed with 53 mg of 10% palladium on activated carbon and hydrogenated at room temperature at a hydrogen pressure of 5 bar. After the reaction had ended, the mixture was filtered from the catalyst and the filtrate was concentrated. The residue was stirred in a mixture of dichloromethane and n-heptane, filtered with suction and dried under reduced pressure. 2-(4-Amino-3-pentafluorosulfanylphenyl)isoindole-1,3-dione 51.7 with the melting point of 176-178° C. was obtained.

Workup

  1. filtrationthe mixture was filtered from the catalyst
  2. concentrationthe filtrate was concentrated
  3. filtrationfiltered with suction
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-cb4024e2c37e48c0a9a875265f1243df
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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