N,N-Dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide → N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

HRID 1840351Notes

Reaction equation

HRID 1840351 reaction equation
[CH3:1][N:2]([CH3:17])[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][N:2]([CH3:17])[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 23447760N,N-Dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide

Product 1

HCID 23447758N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamideYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N,N-Dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide (550 mg, 1.96 mmol) in ethyl acetate, was added 10% Pd/C (550 mg). The mixture was flushed with argon, and then stirred under a hydrogen atmosphere at balloon pressure for 3 hours at room temperature. TLC showed the reaction was not complete. The mixture was filtered through celite and the celite was washed with methanol. The mixture was retreated under the same conditions as mentioned above. After 3 hours, the solvent was evaporated to give the desired product (480 mg, 98%). EI-MS (m/z) 250.82, 252.87 (M+).

Workup

  1. customThe mixture was flushed with argon
  2. filtrationThe mixture was filtered through celite
  3. washthe celite was washed with methanol
  4. waitAfter 3 hours
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2c378cd1d7ed489088d99b50e2b0d845
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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