N,N-dimethyl-1-(3-nitrophenyl)methanesulfonamide → 1-(3-aminophenyl)-N,N-dimethylmethanesulfonamide

HRID 1941908Notes

Reaction equation

HRID 1941908 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Ni].CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 28632733N,N-dimethyl-1-(3-nitrophenyl)methanesulfonamide

Product 1

HCID 432562151-(3-aminophenyl)-N,N-dimethylmethanesulfonamideYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

(3-Nitrophenyl)-N,N-dimethylmethanesulfonamide (2.32 g, 9.5 mmol) was hydrogenated over Raney nickel (0.5 g) in methanol at 50° C. and 70 psi for 4 h, then catalyst was filtered off, washed with warm methanol, combined filtrates were evaporated to give 1.95 g (96%) of (3-aminophenyl)-N,N-dimethylmethanesulfonamide.

Workup

  1. filtrationcatalyst was filtered off
  2. washwashed with warm methanol
  3. customwere evaporated

Sources & evidence

ORD record
ord-4b4947fc59d04593a0abb3be94be815d
Source dataset
uspto-grants-2013_03
Patent number
US08389521B2

Reaction notes

Loading…