N-methyl-2-nitrobenzene-1-sulfonamide → 2-amino-N-methylbenzene-1-sulfonamide

HRID 1487226Notes

Reaction equation

HRID 1487226 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O)(=[O:5])=[O:4]>CO.[Pd]>[NH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[S:3]([NH:2][CH3:1])(=[O:5])=[O:4]

Participants

4

Reactant 1

HCID 264906N-methyl-2-nitrobenzene-1-sulfonamide

Product 1

HCID 11328402-amino-N-methylbenzene-1-sulfonamideYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-methyl-2-nitrobenzenesulfonamide (26 g, 0.12 mol) in methanol (500 mL) was added palladium on carbon (10%, 2 g). The mixture was stirred under an atmosphere of hydrogen at room temperature for 3 hours. The catalyst was filtrated and the filtrate was evaporated to afford the product 2-amino-N-methylbenzenesulfonamide (22 g, yield 98%). 1H NMR (400 MHz, CDCl3) δ ppm 7.45-7.48 (dd, 1H, J=1.6 Hz, 8.0 Hz), 7.24-7.31 (m, 2H), 6.81-6.83 (dd, 1H, J=0.6 Hz, 8.0 Hz), 6.60-6.65 (m, 1H), 5.89 (s, 2H), 2.370-2.374 (d, 3H, J=1.6 Hz).

Workup

  1. filtrationThe catalyst was filtrated
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-daa00be05e744b29b096546a1f676a9a
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

Loading…