Ammonium formate → N-(3-Amino-5-(methylsulfonyl)-phenyl)-methylsulfonamide

HRID 1957962Notes

Reaction equation

HRID 1957962 reaction equation
C[C:2]1[CH:3]=[C:4]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.C([O-])=O.[NH4+]>O1CCOCC1.[Ni]>[NH2:8][C:6]1[CH:5]=[C:4]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:3]=[C:2]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68423293N-(3-methyl-5-nitro-phenyl)-methylsulfonamide

Product 1

HCID 58154480N-(3-Amino-5-(methylsulfonyl)-phenyl)-methylsulfonamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-(3-methyl-5-nitro-phenyl)-methylsulfonamide (0.12 g; 0.4 mmol), ammonium formate (0.26 g; 4 mmol) and Raney-Nickel in 1 mL dioxane was heated at 120° C. in a microwave oven for 20 minutes. The mixture was then filtrated on a celite pad and concentrated. 70 mg (0.35 mmol; 87% yield) of a red oil were obtained.

Workup

  1. filtrationThe mixture was then filtrated on a celite pad
  2. concentrationconcentrated
  3. custom70 mg (0.35 mmol; 87% yield) of a red oil were obtained

Sources & evidence

ORD record
ord-fb985e3e9e5d473684131008127172b7
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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