2-(1H-Indol-5-yl)-N,N-dimethylethenesulphonamide → N,N-Dimethyl-1H-indole-5-ethanesulphonamide
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
Product 1
Reagents, catalysts & solvents 2
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°.