反应详情

温度

15 °C

Conc. nitric acid (33 g) was added dropwise over 3 h to a stirred solution of m-xylidine (40 g, 0.33 mmol) in conc. sulfuric acid (400 g) at <15° C. After complete addition the reaction was stirred at 15° C. for 1 h then poured onto ice (600 mL), stirred for 30 min and filtered. The yellow filter-cake was neutralised with saturated aqueous sodium hydrogen carbonate solution (500 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were dried (Magnesium sulfate), filtered and the solvent removed under vacuum to leave a crude solid. The solid was recrystallised (ethanol-water) to give the product as an orange solid (39 g, 71%, contains 20% di-nitro). IR νmax (Nujol)/cm−1 3469, 3386, 3239, 2956, 2925, 2855, 1719, 1636, 1514, 1461, 1377, 1339, 1297, 1273, 1222, 1170, 1034, 992, 885, 870, 849, 805, 758, 745, 723, 640, 607 and 571; NMR δH (400 MHz; CDCl3) 7.15 (1H, s), 6.87 (1H, s), 4.99 (2H br. s), 2.21 (3H, s), 1.97 (3H, s).

1. additionAfter complete addition the reaction
2. additionthen poured onto ice (600 mL)
3. stirringstirred for 30 min
4. filtrationfiltered
5. filtrationThe yellow filter-cake
6. extractionextracted with ethyl acetate (3×200 mL)
7. dry with materialThe combined organic extracts were dried (Magnesium sulfate)
8. filtrationfiltered
9. customthe solvent removed under vacuum
10. customto leave a crude solid
11. customThe solid was recrystallised (ethanol-water)