N-methanesulfonyl-6-nitroindole → N-methanesulfonyl-6-aminoindole
Reaction equation
[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=2)[CH:7]=[CH:6]1)(=[O:4])=[O:3]>CO.[Pt]=O>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[CH:7]=[CH:6]1)(=[O:4])=[O:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of N-methanesulfonyl-6-nitroindole (2.52 g, 10.5 mmol, from above) and platinum oxide (119 mg, 0.52 mmol) in 100 ml of methanol was hydrogenated in a Parr apparatus for approximately 1 hr until a constant pressure was obtained (42 psi H2 initially). The catalyst was removed by filtration (Whatman GF/F filter) and the filtrate was concentrated by rotary evaporation to give N-methanesulfonyl-6-aminoindole, an oil which solidified on standing under an argon atmosphere.