Hydrochloric Acid → 4-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde

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Reaction Steps

To a stirred solution of 3-3 (16 g, 41.1 mMol) in anhydrous 1,4-dioxane (75 mL) at 0° C. was added 3N HCl (27 mL). The reaction was then allowed to reach room temperature and was stirred for around 3 hours. Upon completion, the reaction was quenched with saturated NaHCO3 solution to reach a pH of >7. The product was extracted into ethyl acetate (3×150 mL). The combined organic layers were washed with brine, dried with Na2SO4 and MgSO4, filtered and concentrated in vacuo to yield 4-(5-chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde 9-1 as a tan solid. LC/MS (M+1) calculated: 345.8; observed: 345.0

Provenance & Evidence