N-Methyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide → N-Methyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

HRID 2301505Notes

Reaction equation

HRID 2301505 reaction equation
[CH3:1][NH:2][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][NH:2][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 18373432N-Methyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide

Product 1

HCID 18373530N-Methyl-3-amino-6-chloro-2-hydroxybenzenesulfonamideYield 127.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-methyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide (140 mg, 0.53 mmol) in ethyl acetate, was added 10% Pd/C (60 mg). The mixture was flushed with argon, 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 (160 mg, >100%). 1H NMR (DMSO-d6): δ 7.95 (bs, 1H), 6.85 (d, 1H), 6.79 (d, 1H), 2.48 (d, 3H).

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-c105672e4e834c46af0a78c49699078a
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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