Hydrochloric Acid → HCID 13247647, compound

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Reaction Steps

A Grignard reagent which is prepared by reacting 1.9 g of magnesium with 15 g of p-chlorobromobenzene in 150 ml of anhydrous ether is added to a suspension of 10.2 g of 3-cyano-2-(1-imidazolyl)pyridine in 200 ml of benzene at 30°-35° C. After the addition is complete, the whole mixture is stirred at room temperature for 1.5 hours. The reaction mixture is treated with an aqueous ammonium chloride solution under ice cooling. To the benzene layer containing the resulting 3-(4-chlorobenzimidoyl)-2-(1-imidazolyl)pyridine is added dilute hydrochloric acid and the mixture is stirred at 35° C. for 10 minutes for hydrolysis. The dilute hydrochloric acid layer is separated and made alkaline with sodium hydroxide and then extracted with chloroform. The chloroform layer is washed with water, dried and concentrated to give 3-(4-chlorobenzoyl)-2-(1-imidazolyl)pyridine as an oil in high yield. This oily product can be used in the next reaction without isolation, but when the oil is treated with toluene, crystallization takes place. Upon recrystallization from toluene the product is obtained as white crystals, melting at 118°-120° C.

Provenance & Evidence