反应详情

温度

120 °C

4-Methoxybenzyl alcohol (4.8 g, 34.7 mmol) was added to sodium (0.8 g, 34.7 mmol) in toluene (100 mL). After most of the sodium has dissolved 6-chloro-3-nitro-2-pyridineamine (5 g, 28.9 mmol) was added and the reaction was heated at 120° C. for 4 h. As there was still some starting material left, more anion of the 4-methoxybenzyl alcohol was prepared in a separate flask (0.6 g of sodium in 30 mL of toluene and 4 g of 4-methoxybenzyl alcohol were used) and added to the reaction at room temperature. The reaction was then stirred at room temperature for 5 h then water (250 mL) was added and the volume reduced to 200 mL. Diethyl ether was then added and the aqueous phase was extracted (3×500 mL). The combined organic phases were dried (MgSO4), filtered and evaporated. The residue was then chromatographed on silica gel, eluting with DCM to afford 4.8 g of the title compound (60%).

1. additionwas added
2. waitleft
3. additionadded to the reaction at room temperature
4. extractionthe aqueous phase was extracted (3×500 mL)
5. dry with materialThe combined organic phases were dried (MgSO4)
6. filtrationfiltered
7. customevaporated
8. customThe residue was then chromatographed on silica gel
9. washeluting with DCM