N-(3-Methoxy-propyl)-C-(3-nitro-phenyl)-methanesulfonamide → C-(3-amino-phenyl)-N-(3-methoxy-propyl)-methanesulfonamide

HRID 1890982Notes

Reaction equation

HRID 1890982 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=1)(=[O:9])=[O:8]>[Ni].CO>[NH2:17][C:13]1[CH:12]=[C:11]([CH2:10][S:7]([NH:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:9])=[O:8])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 59411197N-(3-Methoxy-propyl)-C-(3-nitro-phenyl)-methanesulfonamide

Product 1

HCID 43256757C-(3-amino-phenyl)-N-(3-methoxy-propyl)-methanesulfonamideYield 50.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

N-(3-Methoxy-propyl)-C-(3-nitro-phenyl)-methanesulfonamide (0.31 g, 1.08 mmol) was hydrogenated over Raney nickel (0.05 g) in methanol at 50° C. and 70 psi for 4 h. Then, the catalyst was filtered off, washed with warm methanol, and the combined filtrates were evaporated to give 0.14 g (50%) of C-(3-amino-phenyl)-N-(3-methoxy-propyl)-methanesulfonamide.

Workup

  1. filtrationThen, the catalyst was filtered off
  2. washwashed with warm methanol
  3. customthe combined filtrates were evaporated

Sources & evidence

ORD record
ord-9519bdebdf1346818eb79bdf991f4165
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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