1-(Methanesulfonylmethyl)-4-nitrobenzene → 3-(Methanesulfonylmethyl)aniline

HRID 2281473Notes

Reaction equation

HRID 2281473 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+]([O-])=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].C([O-])=O.[NH4+:18]>CCO.O.CCOC(C)=O.[Fe]>[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[C:10]([CH:9]=[CH:8][CH:7]=1)[NH2:18])(=[O:4])=[O:3]

Participants

7

Reactant 2

HCID 2873701-(Methanesulfonylmethyl)-4-nitrobenzeneHCID 2723923Ammonium formate

Product 1

HCID 219563393-(Methanesulfonylmethyl)anilineYield 71.3%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 1-(methylsulfonylmethyl)-4-nitrobenzene (0.77 g, 3.56 mmol) in EtOH (10 mL) and H2O (5 mL) was added iron (1.0 g, 17.82 mmol) and ammonium formate (2.25 g, 35.6 mmol). After heating at 90° C. for 2 h, it was diluted with EtOAc, washed with saturated NaHCO3, brine, dried and concentrated to give 3-(methylsulfonylmethyl)aniline (0.47 g).

Workup

  1. washwashed with saturated NaHCO3, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b288a3424ec042c19127ed964fe8b35d
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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