[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:19]#[N:20])=[CH:11][C:12]([N+:16]([O-])=O)=[C:13]([CH3:15])[CH:14]=2)=[CH:5][CH:4]=1.[CH3:21]N(C(N(C)C)N(C)C)C.Cl>C1(C)C=CC=CC=1.O.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]3[C:12](=[CH:11][C:10]=2[C:19]#[N:20])[NH:16][CH:21]=[CH:15]3)=[CH:5][CH:4]=1A mixture of 4′-methoxy-5-methyl-4-nitro-biphenyl-2-carbonitrile (118.0 mg, 0.44 mmol) and tris(dimethylamino) methane (128.0 mg, 0.88 mmol) in toluene (15 mL) was heated to reflux for 2 hours. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in EtOH (1 mL) and water (0.10 mL), and treated with iron powder (64.0 mg, 1.15 mmol), followed by concentrated HCl (28.0 mg, 0.29 mmol). The reaction mixture was heated to reflux for an additional 16 hours, and quenched with 1N aqueous NaOH (0.288 mL). The solution was filtered through celite and rinsed with EtOH (10 mL). The filtrate was concentrated in vacuo to give the title compound (35 mg, 49% yield). MS (ES−) 247.1 (M−1)−. 1H NMR (400 MHz, DMSO-d6) δ 7.95 (s, 1H), 7.68 (d, J=2.73 Hz, 1H), 7.66 (s, 1H), 7.48 (d, J=8.59 Hz, 2H), 7.05 (d, J=8.59 Hz, 2H), 6.58 (d, J=2.73 Hz, 1H), 3.82 (s, 3H).
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