[CH:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])=[CH2:2].Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH:1]([C:3]1[CH:4]=[C:5]([NH:6][C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)=[CH2:2]A mixture of 3-vinylaniline (8 g), 2-chloro-3-nitropyridine (10.7 g) and potassium carbonate (18.6 g) in dioxane (80 ml) was stirred under reflux for 5 days. The reaction was extracted with chloroform, washed with water, dried over magnesium sulfate and evaporated. After evaporation of the solvent, crude residue was crystallized from methanol to give 2-(3-vinylphenylamino)-3-nitropyridine as an orange crystals (12.9 g).
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