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

HRID 2301500Notes

Reaction equation

HRID 2301500 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 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N,N-dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide (140 mg, 0.50 mmol) in ethyl acetate, was added 10% Pd/C (50 mg). The mixture was flushed with hydrogen, then stirred under a hydrogen atmosphere at balloon pressure for 1.5 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 (100 mg, 80%). 1H NMR (DMSO-d6): δ 6.87 (d, 1H), 6.80 (d, 1H), 2.82 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-58349c1aaa034db18182f5899171c8ac
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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