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

HRID 396278Notes

Reaction equation

HRID 396278 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 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloro-2-hydroxy-3-nitrobenzenesulfonamide (3 g, 11.9 mmol) in ethyl acetate, was added 10% Pd/C (1.24 g). The mixture was flushed with argon, and then stirred on Parr apparatus at 40 psi for 25 min 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 (2.51 g, 95%). EI-MS (m/z) 222.75, 224.74 (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-04db7c49ee7e46d8a456a65668f1c0a3
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

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