反应详情

温度

80 °C

N-(4-methoxybenzyl)-4-nitropyridin-2-amine (27.8 g, 0.11 mol) and anisole (13 mL, 0.12 mol) were dissolved in trifluoroacetic acid (112 mL) and heated at 80° C. for 2 h. The reaction mixture was allowed to cool to rt and concentrated. Trituration of the resulting residue with EtOAc and hexanes produced a light yellow solid that was isolated via filtration. The filtrate was allowed to stand overnight and a second crop of crystals was obtained. The combined batches of solids were dissolved in 1N NaOH (250 mL) and extracted with EtOAc (2×250 mL). The combined organic solutions were dried over MgSO4, filtered and concentrated to give 2-amino-4-nitropyridine as an orange solid (10.2 g, 67%). LCMS: (FA) ES+ 140.1.

1. temperatureto cool to rt
2. concentrationconcentrated
3. customTrituration of the resulting residue with EtOAc and hexanes produced a light yellow solid
4. customthat was isolated via filtration
5. customa second crop of crystals was obtained
6. extractionextracted with EtOAc (2×250 mL)
7. dry with materialThe combined organic solutions were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated