[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:10])[CH:3]=1.Cl.CN.C([O-])(=O)C.[Na+].[N+:19]([CH3:22])([O-:21])=[O:20]>O.ClCCl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:22][N+:19]([O-:21])=[O:20])=[C:4]([CH3:10])[CH:3]=1A mixture of 4-chloro-2-methylbenzaldehyde (1.56 g, 10.1 mmol), methylamine hydrochloride (0.44 g, 6.5 mmol), and sodium acetate (0.53 g, 6.5 mmol) in nitromethane (4 mL) was vigorously stirred at ambient temperature for 24 hours. The reaction mixture was diluted with water (20 mL) and dichloromethane (40 mL). The organic layer was dried over sodium sulfate and evaporated to afford 4-chloro-2-methyl-1-(2-nitrovinyl)benzene as a light brown solid (1.87 g, 94% yield).
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