N-Methyl-3-nitrobenzenesulfonamide → 3-amino-N-methylbenzenesulfonamide

HRID 902718Notes

Reaction equation

HRID 902718 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)(=[O:5])=[O:4]>CO.CCOC(C)=O.[Pd]>[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1)(=[O:4])=[O:5]

Participants

5

Reactant 1

HCID 579071N-Methyl-3-nitrobenzenesulfonamide

Product 1

HCID 72048903-amino-N-methylbenzenesulfonamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-methyl-3-nitrobenzene sulfonamide (608 mg, 2.8 mmole) in 30 mL of MeOH and 5 mL of EtOAc was treated with 10% Pd/C (100 mg) and hydrogenated at 1 atmosphere H2 pressure for 16 hours. The catalyst was filtered, and the filtrate evaporated. The residue was dissolved in EtOAc, washed with H2O, dried and the solvent removed, and gave the titled product, 498 mg (96%). MS (ESI) 187 (MH+).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with H2O
  5. customdried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-e514e3c898e14189912b279923179e73
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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