Hydrazine → 5-Amino-N-methoxy-2-methylbenzenesulfonamide

HRID 1391534Notes

Reaction equation

HRID 1391534 reaction equation
[CH3:1][O:2][NH:3][S:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=1[CH3:16])(=[O:6])=[O:5].NN>[Pd].C(O)C>[NH2:13][C:11]1[CH:10]=[CH:9][C:8]([CH3:16])=[C:7]([S:4]([NH:3][O:2][CH3:1])(=[O:5])=[O:6])[CH:12]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 59674227N-Methoxy-2-methyl-5-nitrobenzenesulfonamide

Product 1

HCID 596741455-Amino-N-methoxy-2-methylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-Methoxy-2-methyl-5-nitrobenzenesulfonamide (0.5 g, 2 mmol) was combined with 10% palladium on carbon (0.05 g), ethanol (10 mL), and hydrazine (1 mL) and heated at reflux for 18 h. The solution was filtered through celite, concentrated, and purified on silica gel with methanol in dichloromethane. Product was an off white solid (0.28 g, 1.3 mmoL). 1H NMR (300 MHz, d6-DMSO) δ10.3 (s, 1H), 7.11 (s, 1H), 7.02 (d, J=8.2 Hz, 1H), 6.7 (d, J=8.2 Hz, 1H), 5.37 (s, 2H), 3.57 (s, 3H), 2.38 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. filtrationThe solution was filtered through celite,
  4. concentrationconcentrated
  5. custompurified on silica gel with methanol in dichloromethane

Sources & evidence

ORD record
ord-0e1782b7f1f14451bdd0067a8aabece7
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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