(4-Nitrophenyl)acetic acid → HCID 53732243, compound

Participants

Reaction Steps

p-Nitrophenylacetic acid is treated with Vilsmeier reagent to give 3-(dimethylamino)-2-(4-nitrophenyl)-2-propenal. This product is treated with cyanoacetiamide and sodium methoxide to give 1,2-dihydro-5-(4-nitrophenyl)-2-oxo-3-pyridinecarbonitrile. The preceding product is hydrolyzed with 1:1 concentrated hydrochloric acid-acetic acid to give 1,2-dihydro-5-(4-nitrophenyl)-2-oxo-3-pyridinecarboxylic acid. The above product is boiled with quinoline to give 5-(4-nitrophenyl)-2(1H)-pyridone. When the preceding product is treated with phosphorus oxychloride, 2-chloro-5-(4-nitrophenyl)pyridine is obtained. This product is treated with hydrazine to give 2-hydrazino-5-(4-nitrophenyl)pyridine. The above product is treated with ethyl orthoacetate to give the product of the Example.

Provenance & Evidence