Dimethylcarbamoyl Chloride → 7-Chloro-4-phenylquinoline-2-carbonitrile

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Reaction Steps

A solution of 7-chloro-4-phenylquinoline (Example 39, Step 1) (3.0 g, 12.5 mmol) and m-CPBA (2.6 g, 15.0 mmol) in chloroform (50 mL) was stirred at room temperature for 3 h. The reaction was quenched with saturated aqueous NaHCO3 solution and extracted twice with dichloromethane. The combined organic layers were washed with water, brine, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the resulting crude product was dissolved in chloroform (50 mL). N,N-Dimethylcarbamoyl chloride (2.4 mL, 25.0 mmol) and trimethylsilyl cyanide (3.4 mL, 25.0 mmol) were added to this solution and stirred at room temperature for 2 days. Saturated aqueous NaHCO3 solution was added and the mixture stirred for 30 min. The organic layer was removed, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, brine, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the resulting crude product was used in the next step without further purification.

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