2-Nitro-4-(thiophen-2-yl)aniline → 4-(Thiophen-2-yl)benzene-1,2-diamine
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-])=O)[CH:7]=1.[H][H]>[Pd]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH2:13])[C:9]([NH2:10])=[CH:11][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-thienyl-2-nitroaniline (1 equiv, 400 mg, 1.82 mmol) was added 10% Pd/C (0.05 equiv, 97 mg, 0.09 mmol). The resulting suspension was stirred for overnight over 1 atm of hydrogen. The solids were filtered through celite pad and the filtrate was concentrated under vacuum. The crude material was purified by silica gel column chromatography with gradient of MeOH (0-10%) in CH2Cl2 to afford compound 30 (310 mg, 90%) and a white solid. LRMS (ESI): (calc) 190.2 (found) 191.0 (MH)+.