N-benzyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide → N-Benzyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

HRID 2301497Notes

Reaction equation

HRID 2301497 reaction equation
[CH2:1]([NH:8][S:9]([C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([N+:19]([O-])=O)[C:13]=1[OH:22])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[CH2:1]([NH:8][S:9]([C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([NH2:19])[C:13]=1[OH:22])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18373553N-benzyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide

Product 1

HCID 18373453N-Benzyl-3-amino-6-chloro-2-hydroxybenzenesulfonamideYield 86.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-benzyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide (180 mg, 0.52 mmol) in ethyl acetate, was added 10% Pd/C (70 mg). The mixture was flushed with argon, then stirred under a hydrogen atmosphere at balloon pressure for 1 hour 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 (140 mg, 85%). 1H NMR (DMSO-d6): δ 8.73 (t, 1H), 7.24 (m, 5H), 6.78 (d, 1H), 4.09 (d, 2H).

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-fbb9a8006a894737831e410b50ad26e0
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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