2-(1H-Indol-5-yl)-N,N-dimethylethenesulphonamide → N,N-Dimethyl-1H-indole-5-ethanesulphonamide

HRID 982006Notes

Reaction equation

HRID 982006 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[CH:11][S:12]([N:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1>C(O)C.[Pd]=O>[CH3:17][N:15]([CH3:16])[S:12]([CH2:11][CH2:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)(=[O:14])=[O:13]

Participants

4

Reactant 1

HCID 541715032-(1H-Indol-5-yl)-N,N-dimethylethenesulphonamide

Product 1

HCID 13475761N,N-Dimethyl-1H-indole-5-ethanesulphonamideYield 73.1%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of Stage (i) (3.8 g) in ethanol (400 ml) was hydrogenated at room temperature and pressure over 10% palladium oxide on charcoal (50% aq. paste, 0.5 g), for 2 h. The catalyst was filtered off and replaced with a fresh batch (50% aq. paste, 0.5 g) and hydrogenation continued for a further 1 h. The catalyst was filtered off and the filtrate evaporated in vacuo to give a solid (2.8 g) which was recrystallised from a mixture of ethyl acetate and hexane to give the title compound as a solid (2.0 g) m.p. 125°-127°.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-4ad1340e93b541ef9f1eaa45b4a634a6
Source dataset
uspto-grants-1991_02
Patent number
US04994483

Reaction notes

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