(2-Bromo-3-methoxy-6-nitro-phenyl)-phenylamine → 3-Bromo-4-methoxy-N2-phenylbenzene-1,2-diamine
Reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([N+:10]([O-])=O)[C:3]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCOC(C)=O.[Pd]>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([NH2:10])[C:3]=1[NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (2-bromo-3-methoxy-6-nitro-phenyl)-phenylamine (470 mg, 1.81 mmol) in EtOAc (15 mL) was added palladium on carbon (100 mg, 10% by wt) and the reaction mixture stirred at RT under an atmosphere of hydrogen for 16 h. The reaction mixture was filtered and the filtrate concentrated in vacuo to give the title compound as a yellow solid (426 mg, 100%). 1H NMR 400 MHz δ (CDCl3): 7.24-7.17 (2H, m), 6.89-6.83 (1H, m), 6.74-6.72 (1H, m), 6.68-6.63 (2H, m), 5.48 (1H, br s), 3.85 (3H, s).