1-(Cyclopentylsulfonyl)-4-nitrobenzene → 4-(Cyclopentanesulfonyl)aniline

HRID 230833Notes

Reaction equation

HRID 230833 reaction equation
[CH:1]1([S:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(=O)C.[Pd].CO>[CH:1]1([S:6]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 129583201-(Cyclopentylsulfonyl)-4-nitrobenzene

Product 1

HCID 129583154-(Cyclopentanesulfonyl)anilineYield 70.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Intermediate 2 (13.1 g) was dissolved in acetic acid (150 ml) and hydrogenated over palladium on activated carbon (1.6 g) with stirring overnight. The mixture was filtered through Celite filter aid, and the filtrate was evaporated to give a yellow/green oil. The oil was taken up in methanol and an insoluble precipitate filtered off; the filtrate was evaporated in vacuo to give a yellow solid. Trituration with ether and filtration gave the title compound as a pale yellow solid (8.1 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. filtrationfilter aid
  3. customthe filtrate was evaporated
  4. customto give a yellow/green oil
  5. filtrationan insoluble precipitate filtered off
  6. customthe filtrate was evaporated in vacuo
  7. customto give a yellow solid
  8. filtrationTrituration with ether and filtration

Sources & evidence

ORD record
ord-c1252f81086244a2aaf7124be1d79e28
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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