反应详情

温度

50 °C

Aqueous HCl 3N (18.0 mL) was added to a solution of 5-(4-methoxy-benzyl)-5H-dibenzo[b,d]azepine-6,7-dione 7-oxime (10.9 g.) in methanol (150.0 mL). Pd/C (10% weight, 1.08 g) was added to the reaction mixture and the system was stirred under 10 bar H2 at 50° C. for 18 hours. After exchanging H2 for Ar, the reaction mixture was filtered, water (150 mL) was added and methanol was removed under reduced pressure. The aqueous phase was extracted with EtOAc (50.0 mL), the organic phase was washed with water (50.0 mL) and the aqueous phases were extracted separately with the same portion of EtOAc (30.0 mL). Dichloromethane (100.0 mL) was added to the combined aqueous phases and aqueous NaOH 0.9 M (65.5 mL) was added slowly to bring the aqueous phase to pH=ca. 7. After 10 minutes of stirring, the phases were separated; the aqueous phase was extracted with dichloromethane (50.0 mL). The combined organic phases were dried (MgSO4) and concentrated under reduced pressure yielding 7-amino-5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one (9.7 g, 91%) as yellow oil.

1. filtrationthe reaction mixture was filtered
2. additionwater (150 mL) was added
3. custommethanol was removed under reduced pressure
4. extractionThe aqueous phase was extracted with EtOAc (50.0 mL)
5. washthe organic phase was washed with water (50.0 mL)
6. extractionthe aqueous phases were extracted separately with the same portion of EtOAc (30.0 mL)
7. additionDichloromethane (100.0 mL) was added to the combined aqueous phases and aqueous NaOH 0.9 M (65.5 mL)
8. additionwas added slowly
9. stirringAfter 10 minutes of stirring
10. customthe phases were separated
11. extractionthe aqueous phase was extracted with dichloromethane (50.0 mL)
12. dry with materialThe combined organic phases were dried (MgSO4)
13. concentrationconcentrated under reduced pressure