反应详情

温度

0 °C

3-Methoxy-4-(3-morpholin-4-ylpropoxy)-2-nitrobenzonitrile (Step 2, 7.7 g, 24.1 mmol) was suspended in acetic acid (170 mL) and cooled to 0° C. Water (0.4 mL) was added, followed by iron powder (6.7 g, 120 mmol) and the resulting mixture was stirred at room temperature for 4 h at which time the reaction mixture was filtered through a pad of Celite and washed with acetic acid (400 mL). The filtrate was concentrated under reduced pressure to 100 mL and diluted with EtOAc (200 mL) at which time potassium carbonate was added slowly. The resulting slurry was filtered through a pad of Celite washing with EtOAc and water. The layers were separated and the organic layer was washed with saturated sodium bicarbonate solution. The organic layer was separated and passed through a pad of silica gel. The resultant solution was concentrated under reduced pressure to provide the title compound (6.5 g, 92%): 1H NMR (DMSO-d6) δ: 7.13 (1H, d), 6.38 (1H, d), 5.63 (2H, br s), 4.04 (2H, t), 3.65 (3H, s), 3.55 (4H, m), 2.41 (2H, t), 2.38 (4H, m), 1.88 (2H, m).

1. filtrationwas filtered through a pad of Celite
2. washwashed with acetic acid (400 mL)
3. concentrationThe filtrate was concentrated under reduced pressure to 100 mL
4. additiondiluted with EtOAc (200 mL) at which time potassium carbonate
5. additionwas added slowly
6. filtrationThe resulting slurry was filtered through a pad of Celite
7. washwashing with EtOAc and water
8. customThe layers were separated
9. washthe organic layer was washed with saturated sodium bicarbonate solution
10. customThe organic layer was separated
11. concentrationThe resultant solution was concentrated under reduced pressure