1-(Methylsulfonyl)-2-nitrobenzene → 2-Methanesulfonylaniline

HRID 479079Notes

Reaction equation

HRID 479079 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O)(=[O:4])=[O:3]>CO.OS(O)(=O)=O.[Pd]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])(=[O:3])=[O:4]

Participants

5

Reactant 1

HCID 117358061-(Methylsulfonyl)-2-nitrobenzene

Product 1

HCID 2446592-MethanesulfonylanilineYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

2-Methylsulfonylnitrobenzene (13.0 g , 0.065 mol) was suspended in MeOH (140 mL) and 2N H2SO4 (60 mL). 6% Pd/C catalyst (50% wet; 3 g) was added to the suspension and it was hydrogenated at 40 psi in a Parr shaker for 4 hours. The solution was filtered, the catalyst washed twice with 10 mL of MeOH and concentrated on the rotary evaporator to a volume of 80 mL. The suspension was cooled to 5° C. with stirring and 15 mL of aqueous 10 N sodium hydroxide was added and stirred for 30 minutes at 5° C. The solid was filtered, washed with water and dried at 40° C. in vacuum (30 in. Hg) to give 10.5 g (95% yield) of 2-methylsulfonylaniline.

Workup

  1. filtrationThe solution was filtered
  2. washthe catalyst washed twice with 10 mL of MeOH
  3. concentrationconcentrated on the rotary evaporator to a volume of 80 mL
  4. addition15 mL of aqueous 10 N sodium hydroxide was added
  5. stirringstirred for 30 minutes at 5° C
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried at 40° C. in vacuum (30 in. Hg)

Sources & evidence

ORD record
ord-68827b665dee483da77dbc658c82ee35
Source dataset
uspto-grants-2003_11
Patent number
US06642416B2

Reaction notes

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