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

HRID 450051Notes

Reaction equation

HRID 450051 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]>CO.[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

4

Reactant 1

HCID 2584341-(Methylsulfonyl)-4-nitrobenzene

Product 1

HCID 796174-(Methylsulfonyl)anilineYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-methanesulfonyl-4-nitro-benzene (500 mg, 2.48 mmol) in methanol (20 ml) was hydrogenated over 10% Pd—C (100 mg) at atmospheric pressure until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to give a residue, which was recrystallized from ethanol to yield 4-methanesulphonyl-phenylamine (276 mg, 65%) as solid.

Workup

  1. filtrationThe reaction mixture was then filtered over celite and
  2. concentrationconcentrated
  3. customto give a residue, which
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-473679a4a6794f9a8bc325647e04b223
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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