N-methyl-2,3-dihydro-1H-indole-5-sulfonamide → N-methyl-1H-indole-5-sulfonamide

HRID 260648Notes

Reaction equation

HRID 260648 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH2:10][CH2:9]2)(=[O:5])=[O:4]>[Pd].CO>[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2)(=[O:5])=[O:4]

Participants

4

Reactant 1

HCID 6502484N-methyl-2,3-dihydro-1H-indole-5-sulfonamide

Product 1

HCID 14024598N-methyl-1H-indole-5-sulfonamideYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent2×

Procedure

N-methyl-indoline-5-sulfonamide (225 mg, 1.06 mmol), as prepared supra, was mixed with 10% palladium on carbon (84 mg) in methanol (8 ml) and these were refluxed for 23 hours. Additional 10% palladium on carbon (100 mg) and methanol (5 ml) were added, and refluxing continued for an additional 23 hours. The cooled reaction mixture was filtered through a Celite® pad, evaporated, and the crude solid redissolved in tetrahydrofuran and again filtered through a Celite® pad. Evaporation of the filtrate gave 211 mg (95%) of N-methyl-1H-indole-5-sulfonamide. This intermediate could also be produced from the reaction of N-methyl-indoline-5-sulfonamide and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in refluxing ethylene glycol monomethyl ether in 35% yield using known procedures. See, e.g. H. Breuer and H. H ohn, Chimie Therapeutique, 6:659 (1973 ).

Workup

  1. temperaturethese were refluxed for 23 hours
  2. temperaturerefluxing
  3. customThe cooled reaction mixture
  4. filtrationwas filtered through a Celite® pad
  5. customevaporated
  6. dissolutionthe crude solid redissolved in tetrahydrofuran
  7. filtrationagain filtered through a Celite® pad
  8. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-8f9de9ed62224afe89ff8a9fc395c313
Source dataset
uspto-grants-1996_06
Patent number
US05529999

Reaction notes

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