1-(Methylsulfonyl)-4-nitrobenzene → 4-(Methylsulfonyl)aniline

HRID 1883002Notes

Reaction equation

HRID 1883002 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>C1COCC1.C(O)C.[Pd]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 1

HCID 2584341-(Methylsulfonyl)-4-nitrobenzene

Product 1

HCID 796174-(Methylsulfonyl)anilineYield 91%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(methylsulfonyl)nitrobenzene (6.26 g, 31.1 mmol) in THF (200 mL) and ethanol (100 mL) was placed in a high pressure reaction vessel and to this solution was added 5% Pd/C (1.6 g). The vessel was shaken for 8 h under an atmosphere of hydrogen (60 psi). The solution was then filtered through diatomaceous earth, partially concentrated in vacuo, and diluted with diethyl ether. The resulting precipitate was filtered and dried in vacuo to give 4.84 g (91%) of a tan solid.

Workup

  1. filtrationThe solution was then filtered through diatomaceous earth
  2. concentrationpartially concentrated in vacuo
  3. additiondiluted with diethyl ether
  4. filtrationThe resulting precipitate was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a8b1540d45584116a24ac6989349662f
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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