反应详情

温度

85 °C

To a solution of the crude (E)-ethyl 2-(cyanomethyl)-3-(3-nitro-4′-(pyrrolidine-1-carbonyl)biphenyl-4-yl)acrylate in AcOH (650 mL) was added iron (29.1 g, 521 mmol) at room temperature. The resulting mixture was heated at 85° C. for 4 h. The reaction mixture was cooled to room temperature and diluted with CH2Cl2 (250 mL). The solids were filtered off and washed with CH2Cl2 (200 mL). The filtrate was concentrated under reduced pressure to give the crude material that was diluted with CH2Cl2 (250 mL) again. To this mixture was slowly added sat'd aq Na2CO3 (˜330 mL) with vigorous stirring until it became basic (pH ˜9-10). The resulting mixture was filtered off and washed with CH2Cl2 (˜250 mL). The aqueous layer was separated and extracted with CH2Cl2 (2×150 mL). The combined organic layers were washed with brine, dried over MgSO4, and filtered to give the crude material that was diluted with EtOAc (70 mL). The mixture was kept for 16 h at room temperature. The suspension was filtered. The solids filtered off were washed with EtOAc (100 mL) to give the crude product that was washed with a small amount of CH2Cl2 to afford 20 g (62% based on 95% purity) of (1E,4E)-ethyl 2-amino-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxylate.

1. temperatureThe reaction mixture was cooled to room temperature
2. filtrationThe solids were filtered off
3. washwashed with CH2Cl2 (200 mL)
4. concentrationThe filtrate was concentrated under reduced pressure
5. customto give the crude material that
6. additionTo this mixture was slowly added
7. filtrationThe resulting mixture was filtered off
8. washwashed with CH2Cl2 (˜250 mL)
9. customThe aqueous layer was separated
10. extractionextracted with CH2Cl2 (2×150 mL)
11. washThe combined organic layers were washed with brine
12. dry with materialdried over MgSO4
13. filtrationfiltered
14. customto give the crude material that
15. filtrationThe suspension was filtered
16. filtrationThe solids filtered off
17. washwere washed with EtOAc (100 mL)
18. customto give the crude product that
19. washwas washed with a small amount of CH2Cl2