A new method for the synthesis of 5-Amino-[3,4'-bipyridin]-6-(1H)-one (Amrinone) by use of α-Substituted Acetamides

Document Type : Original Article

Authors

1 Department of chemistry, Payam noor university, Tehran, Iran

2 Department of chemistry, Faculty of science, Ferdowsi University of Mashhad, Mashhad, Iran

Abstract

This research aims to develop novel synthetic methods for amrinone through two distinct synthetic pathways. The first pathway, based on established chemical protocols, involves a four-step reaction sequence. Initially, pyridine-4-acetic acid reacts with the Vilsmeier reagent, followed by condensation with cyanoacetamide under alkaline conditions. The nitrile group is then hydrolyzed under acidic conditions, and the final step involves a Hofmann rearrangement. The structure of the synthesized amrinone was confirmed using FT-IR and 1HNMR spectroscopy. The second pathway begins with the one-pot synthesis of 2-nitroacetamide, which is subsequently reacted with 3-(dimethylamino)-2-(pyridin-4-yl)acrolein under alkaline conditions to produce 5-nitro-[3’,4’-bipyridin]-6-(1H)-one, an amrinone precursor. This method employs ethanol as a solvent and cost-effective potassium hydroxide as the base. The nitro group in the precursor is reduced using hydrogen gas in the presence of a metal catalyst, yielding amrinone with high purity and efficiency. The proposed methods offer several advantages, including fewer reaction steps, simplified purification, use of inexpensive and readily available starting materials and solvents, enhanced reaction speed, and improved yields. Overall, this study demonstrates that the newly developed synthetic approaches provide a more efficient and practical alternative to existing methods, significantly enhancing the production of amrinone.

Keywords

Main Subjects

Applied Chemistry Today
Volume 20, Issue 76
December 2025
Pages 135-152

Files

Share

How to cite

Statistics