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

HRID 2301493Notes

Reaction equation

HRID 2301493 reaction equation
[Cl:1][C:2]1[C:7]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:6]([OH:12])[C:5]([N+:13]([O-])=O)=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[NH2:13][C:5]1[C:6]([OH:12])=[C:7]([S:8]([NH2:11])(=[O:10])=[O:9])[C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 1

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

Product 1

HCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamideYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloro-2-hydroxy-3-nitrobenzenesulfonamide (1.1 g, 4.36 mmol) in ethyl acetate, was added 10% Pd/C (500 mg). The mixture was flushed with argon, 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 (0.9g, 93%). EI-MS (m/z) 221.1, 223.1 (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-546c0dbfdfa94ca1a5052732d02f4dd2
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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