(2-Fluoro-6-nitrophenyl)phenylamine → 3-Fluoro-N2-phenylbenzene-1,2-diamine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of (2-fluoro-6-nitrophenyl)phenylamine (558 mg, 6.57 mmol) and 10% Pd/C (115 mg) in IMS (20 mL) was degassed with a stream of nitrogen and stirred at RT under a hydrogen atmosphere for 2 h. The suspension was then filtered through a PTFE frit and the filtrate was concentrated in vacuo affording 3-Fluoro-N2-phenylbenzene-1,2-diamine as a white solid (468 mg, 96%). 1H NMR (CDCl3, 400 MHz): δ 7.24-7.16 (2H, m), 7.04-6.96 (1H, m), 6.83 (1H, t, J=7.37 Hz), 6.66 (2H, d, J=7.95 Hz), 6.59-6.48 (2H, m), 5.16 (1H, bs), 3.96 (2H, s).