HCID 18542531, compound → 2,3-Dihydro-1-benzothiophen-5-amine 1,1-dioxide
Reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[S:8](=[O:12])(=[O:11])[CH:9]=[CH:10][C:6]=2[CH:5]=1)([O-])=O>[Pd].CCO.C1COCC1>[O:11]=[S:8]1(=[O:12])[CH2:9][CH2:10][C:6]2[CH:5]=[C:4]([NH2:1])[CH:14]=[CH:13][C:7]1=2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Palladium on carbon (25 mg) was placed under an inert atmosphere and suspended in 1:1 v/v EtOH/THF (10 mL). A solution of 5-nitrobenzo[b]thiophene 1,1-dioxide (250 mg, 1.18 mmol) in EtOH/THF (1:1) was then added, and the reaction mixture placed under H2 atmosphere (1 Atm pressure) and stirred at RT for 3 h. Reaction is filtered through a Celite pad and washed well with MeOH to obtain the title compound (200 mg, 92%) as a brown solid: TLC (10% MeOH/DCM w/5% NH4OH), Rf=0.40; LC MS m/z 184.1 (MH+).