2-(4-Fluorophenyl)acetic acid → HCID 54517698, compound

Participants

Reaction Steps

In a manner similar to Example 1, p-fluorophenyl acetic acid is treated with Vilsmeier reagent to produce 3-(dimethylamino)-2-(4-fluorophenyl)-2-propenal. Treatment of this product with cyanoacetamide and sodium methoxide provides 1,2-dihydro-5-(4-fluorophenyl)-2-oxo-3-pyridinecarbonitrile. Hydrolysis of this product with acid gives 1,2-dihydro-5-(4-fluorophenyl)-2-oxo-3-pyridinecarboxylic acid. Treatment of this product with quinoline affords 5-(4-fluorophenyl)-2(1H)-pyridone, which is reacted with phosphorus oxychloride to give 2-chloro-5-(4-fluorophenyl)pyridine. Treatment of the above product with hydrazine produces 2-hydrazino-5-(4-fluorophenyl)pyridine. Treatment of this product with ethyl orthoacetate produces 6-(4-fluorophenyl)-3-methyl-1,2,4-triazolor[4,3-a]pyridine which yields the product of the Example on hydrogenation.

Provenance & Evidence