N-Methyl-N-(2-nitrophenyl)methanesulfonamide → N-(2-Aminophenyl)-N-methylmethanesulfonamide

HRID 629196Notes

Reaction equation

HRID 629196 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)[S:3]([CH3:6])(=[O:5])=[O:4]>CO.[Pd]>[NH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4]

Participants

4

Reactant 1

HCID 13314625N-Methyl-N-(2-nitrophenyl)methanesulfonamide

Product 1

HCID 13314626N-(2-Aminophenyl)-N-methylmethanesulfonamideYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-methyl-N-(2-nitrophenyl)methanesulfonamide (900 mg, 3.91 mmol) in methanol (5 mL) was added palladium on carbon (10% by weight, 416 mg, 0.39 mmol). The solution was purged with hydrogen and then stirred for 4 hours under 1 atm of hydrogen. The crude reaction was filtered, concentrated and purified by chromatography to provide N-(2-aminophenyl)-N-methylmethanesulfonamide (540 mg, 60% yield). Product not characterized.

Workup

  1. customThe solution was purged with hydrogen
  2. customThe crude reaction
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-80b4813db832440eb10f5698c82da5a1
Source dataset
uspto-grants-2016_04
Patent number
US09315494B2

Reaction notes

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