反应详情

5-Bromo-N-(4-chlorophenyl)-2-methoxybenzamide (9.0 g) obtained in step C, and 7.8 g of zinc cyanide were dissolved in 100 mL of N,N-dimethylformamide. The N,N-dimethylformamide was degassed under reduced pressure, and then the interior of the reactor was purged with nitrogen. After 2.3 g of tetrakistriphenylphosphine palladium was added, the N,N-dimethylformamide was degassed again under reduced pressure, and then the interior of the reactor was purged with argon. This solution was stirred for 2 hours and a half at 100° C., whereafter the solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The insolubles were removed by filtration, and washed with ethyl acetate. The filtrate and the washings were combined, 100 mL of water was added, and then the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate. After the respective organic layers were combined, the combined organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was separated by filtration, and then washed with ethyl acetate. The filtrate and the washings were combined, and ethyl acetate was distilled off under reduced pressure. The resulting residue was washed with methanol. The resulting solid was dried under reduced pressure to obtain 4.9 g (64%) of 5-cyano-N-(4-chlorophenyl)-2-methoxybenzamide.

1. customThe N,N-dimethylformamide was degassed under reduced pressure
2. customthe interior of the reactor was purged with nitrogen
3. additionAfter 2.3 g of tetrakistriphenylphosphine palladium was added
4. customthe N,N-dimethylformamide was degassed again under reduced pressure
5. customthe interior of the reactor was purged with argon
6. distillationa half at 100° C., whereafter the solvent was distilled off under reduced pressure
7. dissolutionthe residue was dissolved in ethyl acetate
8. customThe insolubles were removed by filtration
9. washwashed with ethyl acetate
10. addition100 mL of water was added
11. customthe organic layer was separated
12. extractionThe aqueous layer was extracted twice with ethyl acetate
13. washthe combined organic layer was washed with a saturated aqueous solution of sodium chloride
14. dry with materialdried over anhydrous sodium sulfate
15. customThe anhydrous sodium sulfate was separated by filtration
16. washwashed with ethyl acetate
17. distillationethyl acetate was distilled off under reduced pressure
18. washThe resulting residue was washed with methanol
19. customThe resulting solid was dried under reduced pressure