N,N-Dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide → N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

HRID 1840331Notes

Reaction equation

HRID 1840331 reaction equation
[CH3:1][N:2]([CH3:17])[S:3]([C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([N+:13]([O-])=O)[C:7]=1[OH:16])(=[O:5])=[O:4]>C(OCC)(=O)C.[Pd]>[CH3:1][N:2]([CH3:17])[S:3]([C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([NH2:13])[C:7]=1[OH:16])(=[O:5])=[O:4]

Participants

4

Reactant 1

HCID 23447760N,N-Dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide

Product 1

HCID 23447758N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamideYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N,N-dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide (2.3 g, 8.2 mmol) in ethyl acetate, was added 10% Pd/C (2.0 g). The mixture was flushed with argon, and then stirred under a hydrogen atmosphere at balloon pressure for 3 hours at room temperature. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated to give the desired product (2.0 g, 97%). EI-MS (m/z) 249.5 (M−).

Workup

  1. customThe mixture was flushed with argon
  2. filtrationThe mixture was filtered through celite
  3. washthe celite was washed with methanol
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-fffc40ddbe2949f8a1f0f5ad8bcb70f4
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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