Dimethylformamide → 5-cyano-N-(4-chlorophenyl)-2-methoxybenzamide

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Reaction Steps

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.

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