1-(Methanesulfonylmethyl)-3-nitrobenzene → 3-(Methanesulfonylmethyl)aniline

HRID 1890990Notes

Reaction equation

HRID 1890990 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)(=[O:4])=[O:3]>[Ni].CO>[CH3:1][S:2]([CH2:5][C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 179084331-(Methanesulfonylmethyl)-3-nitrobenzene

Product 1

HCID 219563393-(Methanesulfonylmethyl)anilineYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1-Methanesulfonylmethyl-3-nitro-benzene (4.3 g; 20 mmol) was hydrogenated over Raney nickel (0.5 g) in methanol at 50° C. and 70 psi for 4 h. The catalyst was filtered out, washed with warm methanol, and the combined filtrates were evaporated to give 3.33 g (90%) of 3-methanesulfonylmethyl-phenylamine as colorless solid.

Workup

  1. filtrationThe catalyst was filtered out
  2. washwashed with warm methanol
  3. customthe combined filtrates were evaporated

Sources & evidence

ORD record
ord-9d85d7eb202c46f085d1b4cde9e61409
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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