N-isopropyl-2-nitrobenzenesulfonamide → 2-Amino-N-isopropylbenzenesulfonamide

HRID 1887710Notes

Reaction equation

HRID 1887710 reaction equation
[CH:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-])=O)(=[O:7])=[O:6])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[NH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:5]([NH:4][CH:1]([CH3:3])[CH3:2])(=[O:7])=[O:6]

Participants

5

Reactant 2

HCID 4154456N-isopropyl-2-nitrobenzenesulfonamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 167834652-Amino-N-isopropylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To N-isopropyl-2-nitrobenzenesulfonamide (774 mg) in methanol (50 mL) was added Pd/C (10% Pd in carbon, 150 mg, 19 wt %) under argon protection. A hydrogen balloon was used as the hydrogen source. The reaction was stirred at room temperature overnight. The mixture was filtered through celite and the celite pad was washed several times. The solvent was removed and the crude was purified by silica gel chromatography to obtain the desired product 2-amino-N-isopropylbenzenesulfonamide (quantitative yield).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe celite pad was washed several times
  3. customThe solvent was removed
  4. customthe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ad18248975df4150a1fb470bd327ec34
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

Loading…