(4-Nitrophenyl)methanesulfonamide → 1-(4-Aminophenyl)methanesulfonamide

HRID 583910Notes

Reaction equation

HRID 583910 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH2:8][S:9]([NH2:12])(=[O:11])=[O:10])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]([CH2:8][S:9]([NH2:12])(=[O:10])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 2755281(4-Nitrophenyl)methanesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 108214071-(4-Aminophenyl)methanesulfonamideYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To 10% palladium on charcoal catalyst (3 g, 50% wet with water) under a nitrogen atmosphere was added a solution of 4-nitro-benzylsulfonamide (17.53 g, 81.1 mmol). in dimethylformamide (175 ml). The atmosphere of nitrogen was replaced with hydrogen and the mixture stirred vigourously for 5 h. The atmosphere was replaced with nitrogen and the mixture filtered through celite. The solvent was removed in vacuo and the residue triturated with diethylether to give a dark brown solid (14.7 g). The solid was heated in acetonitrile (440 ml) and filtered whilst hot (to remove excess catalyst). The filtrate was allowed to cool and the precipitate filtered off and dried in vacuo to give the title compound as a beige solid (12.32 g, 82%). δH [2H6]—DMSO 4.05 (2H, s); 5.11 (2H, s); 6.53 (2H, d, 8.2 Hz); 6.63 (2H, s); 7.01(2H,d, 8.2 Hz).

Workup

  1. filtrationthe mixture filtered through celite
  2. customThe solvent was removed in vacuo
  3. customthe residue triturated with diethylether

Sources & evidence

ORD record
ord-9bbd69963680421094a9a4471d347832
Source dataset
uspto-grants-2005_08
Patent number
US06924297B2

Reaction notes

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