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

HRID 2381699Notes

Reaction equation

HRID 2381699 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-7ac148975bbb485aa6975dc418eeb50b
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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