反应详情

温度

95 °C

Iron powder (21.05 g, 377 mmol), water (8 mL), and concentrated hydrochloric acid (0.63 mL, ˜7.5 mmol) were added consecutively to a solution of methyl 4-formyl-3-nitrobenzoate (8.04 g, 38.4 mmol) in EtOH (100 mL). The mixture was stirred at 95° C. for 1.5 h. Acetophenone (4.4 mL, 37.7 mmol) and solid KOH (6.344 g, 113 mmol) were then added with caution. This mixture was stirred at 95° C. for another 5 h. The inorganic solids were filtered off when still warm and the filtrate was acidified to pH=˜1.0 with 4 N HCl(aq). The solvents were removed and water (10 mL) was added. The product was extracted into THF (100 mL×3), dried over MgSO4, filtered, concentrated to afford the desired product as HCl salt; 1H-NMR (CD3OD, 400 MHz) δ 7.73-7.80 (m, 3 H), 8.17-8.20 (m, 2 H), 8.40-8.48 (m, 3 H), 9.02 (d, J=0.8 Hz, 1H), 9.17 (d, J=8.8 Hz, 1 H). MS (ES+): m/z 250 [MH+]. HPLC: tR=3.18 min (OpenLynx, polar—5 min).

1. stirringThis mixture was stirred at 95° C. for another 5 h
2. filtrationThe inorganic solids were filtered off when
3. temperaturestill warm
4. customThe solvents were removed
5. additionwater (10 mL) was added
6. extractionThe product was extracted into THF (100 mL×3)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated