6-Chloro-2-hydroxy-3-nitrobenzenesulfonamide → 3-Amino-6-chloro-2-hydroxy-benzenesulfonamide

HRID 432604Notes

Reaction equation

HRID 432604 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13]>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13]

Participants

4

Reactant 1

HCID 112768176-Chloro-2-hydroxy-3-nitrobenzenesulfonamide

Product 1

HCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamideYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-hydroxy-3-nitro-6-chlorobenzenesulfonamide (1.1 g, 4.36 mmol) in ethyl acetate, was added 10% Pd/C (500 mg). The mixture was flushed with hydrogen, and then stirred under a hydrogen atmosphere at balloon pressure for 4 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 (91%). EI-MS (m/z) 221.1, 223.1 (M).

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-9aef4d97649e41189485526750ca483e
Source dataset
uspto-grants-2003_12
Patent number
US06664259B2

Reaction notes

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