2-Chloro-3-nitropyridine → N-(4-Methylphenyl)-3-nitropyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

2-chloro-3-nitropyridine (100 mg, 0.63 mmol) was dissolved in dioxane (4 mL) in a round bottom flask to which p-tolylaniline (68 mg, 0.63 mmol) was added followed by addition of diisopropylethylamine (0.22 mL). The reaction mixture was heated to 80° C. for 24 hours and stopped when complete as observed by LCMS. After cooling to room temperature, the solvent was removed under reduced pressure to afford an oily residue. The residue was dissolved in ethyl acetate (20 mL) and washed with water and brine (5 mL each respectively). The organic phase was separated and dried over Na2SO4. After filtration the solvent was removed under reduced pressure. The crude product was carried on to the next step without further purification. LCMS [M+H]: 230.

Provenance & Evidence