N-Methyl-4-nitrobenzeneethanesulfonamide → 4-Amino-N-methylbenzeneethanesulfonamide

HRID 1508079Notes

Reaction equation

HRID 1508079 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)(=[O:5])=[O:4]>CO.[Pd]>[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)(=[O:4])=[O:5]

Participants

4

Reactant 1

HCID 13475730N-Methyl-4-nitrobenzeneethanesulfonamide

Product 1

HCID 134757684-Amino-N-methylbenzeneethanesulfonamideYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 402 mg (1.65 mmol) of 2-(4-nitro-phenyl)-ethanesulfonic acid methylamide (as prepared in the previous step) in MeOH (30 mL) was hydrogenated over 10% Pd/C (Degussa type E101-NE/W, Aldrich, 50% by weight water) at 20 psi of H2 for 19 h. The reaction mixture was filtered through Celite, and the filter cake was washed with MeOH. Solvents were evaporated in vacuo. Silica gel chromatography of the residue on a 25-g Varian MegaBond Elut SPE column with 50% EtOAc-hexane afforded 318 mg (90%) of the title compound as a white solid: 1H-NMR (CD3CN; 400 MHz): δ 7.01 (d, 2H, J=8.4 Hz), 6.61 (d, 2H, J=8.4 Hz), 5.00-4.92 (br s, 1H), 4.12-4.02 (br s, 2H), 3.24-3.17 (m, 2H), 2.92-2.86 (m, 2H), 2.67 (s, 3H, J=5.2 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH
  3. customSolvents were evaporated in vacuo

Sources & evidence

ORD record
ord-83808cc5813940f59baec2c593a6c646
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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