反应详情

To a stirred solution of 3.3 g of crude [2-[[3-(dimethylamino)propyl](3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone obtained in Example (8c) in 20 ml of acetic acid at 65° C. was added portionwise 6.6 g of iron powder. The reaction was exothermic at the beginning, the temperature rising to 90° C. Thereafter the temperature was controlled at 85° C. for 1 hr. The mixture was filtered through celite and washed with acetic acid and methanol. The filtrate and washes were combined and evaporated and the residue was dissolved in methanol. The solution was filtered to remove insoluble iron acetate. The filtrate was evaporated and the residue dissolved in water/methylene chloride and made basic with sodium hydroxide and potassium carbonate. The mixture was mixed with celite and filtered through celite. The aqueous layer of the filtrate was extracted twice with methylene chloride which had been used to wash the cake. The combined methylene chloride solution was washed once with NaCl solution, dried and treated with charcoal, filtered and evaporated to give a black foam weighing 1.63 g (46%). The foam was dissolved in isopropyl alcohol. The solution was treated with charcoal and the mixture was filtered into a solution of 0.7 g fumaric acid in isopropyl alcohol. This solution was again treated with charcoal and filtered. Chemical ionization mass spectral analysis and thin-layer chromatography confirmed the presence of the title compound.

1. customrising to 90° C
2. filtrationThe mixture was filtered through celite
3. washwashed with acetic acid and methanol
4. customevaporated
5. dissolutionthe residue was dissolved in methanol
6. filtrationThe solution was filtered
7. customto remove insoluble iron acetate
8. customThe filtrate was evaporated
9. dissolutionthe residue dissolved in water/methylene chloride
10. additionThe mixture was mixed with celite
11. filtrationfiltered through celite
12. extractionThe aqueous layer of the filtrate was extracted twice with methylene chloride which
13. washto wash the cake
14. washThe combined methylene chloride solution was washed once with NaCl solution
15. customdried
16. additiontreated with charcoal
17. filtrationfiltered
18. customevaporated
19. customto give a black foam
20. filtrationthe mixture was filtered into a solution of 0.7 g fumaric acid in isopropyl alcohol
21. additionThis solution was again treated with charcoal
22. filtrationfiltered