N-Methyl-3-nitrobenzenesulfonamide → 3-amino-N-methylbenzenesulfonamide

HRID 255041Notes

Reaction equation

HRID 255041 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)(=[O:5])=[O:4]>C(OCC)(=O)C.[Pd]>[NH2:12][C:8]1[CH:7]=[C:6]([S:3]([NH:2][CH3:1])(=[O:5])=[O:4])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 579071N-Methyl-3-nitrobenzenesulfonamide

Product 1

HCID 72048903-amino-N-methylbenzenesulfonamideYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A reaction vessel charged with the prepared N-methyl-3-nitro-benzenesulfonamide (4.2 g, 19.42 mmol) in 150 ml of ethyl acetate was further charged with 450 mg of 10% palladium on carbon. The reaction mixture was stirred under hydrogen atmosphere for 48 h, then was filtered through a pad of silica gel washing with EtOAc, and the filtrate was concentrated under reduced pressure. The free base was acidified to give 2.1 g, (˜11 mmol, 58% yield) of the title compound (a compound of formula (W) wherein R is methyl) as its HCl-salt.

Workup

  1. filtrationwas filtered through a pad of silica gel washing with EtOAc
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b31f7b5e88454c6f98bf455866d30dfb
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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