3-Nitro-5-pentafluorosulfanylbenzoic Acid → 3-Amino-5-pentafluorosulfanylbenzoic acid

HRID 658011Notes

Reaction equation

HRID 658011 reaction equation
[F:1][S:2]([F:18])([F:17])([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[C:6]([OH:8])=[O:7].[H][H]>CO.[Ni]>[NH2:12][C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([S:2]([F:18])([F:1])([F:15])([F:16])[F:17])[CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 596421523-Nitro-5-pentafluorosulfanylbenzoic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 580857063-Amino-5-pentafluorosulfanylbenzoic acidYield 86.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Subsequently, the 3-pentafluorosulfanyl-5-nitrobenzoic acid (5 g) was dissolved in methanol (300 ml), Raney nickel (about 750 mg) was added and hydrogenation was effected under a hydrogen atmosphere (hydrogen balloon). After 3 h, the catalyst was filtered off and the filter residue was washed thoroughly with methanol. The filtrate was concentrated and dried. The residue was purified using silica gel (2×50 g cartridge, n-heptane/EA gradient of 0-100% within 60 min). 3.9 g of the title compound were obtained.

Workup

  1. filtrationthe catalyst was filtered off
  2. washthe filter residue was washed thoroughly with methanol
  3. concentrationThe filtrate was concentrated
  4. customdried
  5. customThe residue was purified
  6. customsilica gel (2×50 g cartridge, n-heptane/EA gradient of 0-100% within 60 min)

Sources & evidence

ORD record
ord-48ab0642f25b4116904aac37c591f323
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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