2-Nitro-N-propylbenzenesulfonamide → 2-amino-N-propylbenzenesulfonamide

HRID 1487228Notes

Reaction equation

HRID 1487228 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][CH3:16])(=[O:12])=[O:11])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][CH3:16])(=[O:12])=[O:11]

Participants

4

Reactant 1

HCID 23033002-Nitro-N-propylbenzenesulfonamide

Product 1

HCID 47136732-amino-N-propylbenzenesulfonamideYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-N-propylbenzenesulfonamide (8.64 g, 0.035 mol) in methanol (100 mL) was added palladium on carbon (10%, 3.5 g). The mixture was stirred under an atmosphere of hydrogen for 12 hours. The catalyst was removed by filtration and the filtrate was evaporated. The solid residue was washed with ether to afford 2-amino-N-propylbenzenesulfonamide (7.45 g, yield 98.3%), which was dissolved in ether, and bubbled in hydrochloride (gas) to afford the product 2-amino-N-propylbenzenesulfonamide hydrochloride (8.61 g, yield 98.4%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.14 (br s, 3H), 7.50-7.62 (m, 2H), 7.26-7.30 (dt, 1H, J=1.6 Hz, 7.6 Hz), 6.88-6.90 (d, 1H, J=8.0 Hz), 6.67-6.71 (m, 1H), 2.61-2.65 (t, 2H, J=7.2 Hz), 1.28-1.37 (sext, 2H, J=7.2 Hz), 0.72-0.76 (t, 3H, J=7.6 Hz).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. washThe solid residue was washed with ether

Sources & evidence

ORD record
ord-e8f8a15e944447e3a46f211125f1ab19
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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