反应详情

温度

18 °C

Imipramine (4a) (1.925 g, 6.87 mmol) was dissolved in 32 mL acetic acid and cooled to 18° C. Concentrated nitric acid (0.79 mL, 13 mmol) in 1.1 mL acetic acid was added dropwise, with stirring, keeping reaction at 17°-18° C., then reaction stirred at that temperature for an additional 20 minutes. The reaction was then poured into 130 mL of 0.15M HCl and washed with Et2O (2×85 mL), the pH was adjusted to 13 with 10N NaOH and extracted with CHCl3 (4×100 mL). The CHCl3 extracts were combined, washed with 85 mL brine, dried over Na2SO4, and solvent removed in vacuo. The residue was purified by column chromatography, eluting with THF/Hex/NH4OH (70/30/0.4) to yield 1.145 g (51%) of the desired 2-nitroimipramine (4b) as a red oil. 1H NMR (200 MHz, CDCl3) d 8.0-7.9 (m, 2H), 7.3-7.0 (m, 5H), 3.9 (t, 2H), 3.2 (s, 4H), 2.3 (t, 2H), 2.1 (s, 6H), 1.7 (p, 2H); mass spec (FAB) (M+H)+ 326.

1. customreaction at 17°-18° C.
2. customreaction
3. stirringstirred at that temperature for an additional 20 minutes
4. washwashed with Et2O (2×85 mL)
5. extractionextracted with CHCl3 (4×100 mL)
6. washwashed with 85 mL brine
7. dry with materialdried over Na2SO4, and solvent
8. customremoved in vacuo
9. customThe residue was purified by column chromatography
10. washeluting with THF/Hex/NH4OH (70/30/0.4)