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With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃;
Step 5: 8-Chloro-6-methoxyquinoline To a solution of 3.3 g of 8-chloro-6-hydroxyquinoline (Step 4, 3.3 g) in dimethylformamide was added K2CO3 (3.8 g), followed by iodomethane (5.2 g). The mixture was stirred at room temperature overnight. Water was then added and the aqueous mixture was extracted with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using 100% CH2Cl2, to give 2.2 g of the desired product as a beige solid; MP=74-75 C.; MS (ES) m/z (relative intensity): 194 (M+H)+ (100).
With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃;
Example 11 Intermediate 11-8-chloro-6-methoxy-quinoline To a solution of 15 g of 8-chloro-6-hydroxy-quinoline in (50 ml) DMF, 23 g of K2CO3 were added followed by 18 g iodomethane. The mixture was stirred at room temperature overnight. Water was added and the product was extracted with CH2Cl2 dried and the solvent removed. The crude product was filtered through 250 ml of silica gel using 50% ethyl acetate/hexane to give 11 g of the desired product.
With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20.0℃;
To a solution of 15 g of 8-chloro-6-hydroxy-quinoline in (50 ml) DMF, 23 g OF K2C03 were added followed by 18 g iodomethane. The mixture was stirred at room temperature overnight. Water was added and the product was extracted with CH2C12 dried and the solvent removed. The crude product was filtered through 250 ml of silica gel using 50% ethyl acetate/hexane to give 11 g of the desired product.
With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃;
To a solution of 3.3 g of 8-chloro-6-hydroxyquinoline (Step 1, 3.3 g) in dimethylformamide was added K2CO3 (3.8 g), followed by iodomethane (5.2 g). The mixture was stirred at room temperature overnight. Water was then added and the aqueous mixture was extracted with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using 100% CH2Cl2, to give 2.2 g of the desired product as a beige solid; MP=74-75 C.; MS (ES) m/z (relative intensity): 194 (M+H)+ (100).
With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃;
Step 5: 8-Chloro-6-methoxyquinolineTo a solution of 3.3 g of 8-chloro-6-hydroxyquinoline (Step 4, 3.3 g) in dimethylformamide was added K2CO3 (3.8 g), followed by iodomethane (5.2 g). The mixture was stirred at room temperature overnight. Water was then added and the aqueous mixture <n="30"/>was extracted with CH2CI2. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using 100% CH2Cl2, to give 2.2 g of the desired product as a beige solid; MP = 74-75C; MS (ES) m/z (relative intensity): 194 (M+H)+ (100).
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