For chemists and material scientists involved in pharmaceutical development, a deep understanding of the synthesis and properties of key intermediates is essential. 4-(4-Aminophenoxy)-N-methylpicolinamide (CAS 284462-37-9) is one such compound, recognized for its utility as a building block in complex organic synthesis, particularly for drug discovery. This article explores its common synthesis routes and notable chemical characteristics, providing insights for researchers seeking to procure or utilize this valuable molecule.

The synthesis of 4-(4-Aminophenoxy)-N-methylpicolinamide typically involves the coupling of a 4-aminophenol derivative with a suitable picolinamide precursor. One common approach involves reacting 4-aminophenol with a protected or activated 4-chloro-2-pyridinecarboxylic acid derivative, followed by amidation. For instance, a widely cited method involves the reaction of 4-aminophenol with (4-chloro(2-pyridyl))-N-methyl carboxamide in the presence of a base such as potassium tert-butoxide and potassium carbonate, often in a polar aprotic solvent like DMF, and then heating to facilitate the ether linkage formation. The resulting crude product is then purified, often via column chromatography, to yield the desired compound.

The chemical properties of 4-(4-Aminophenoxy)-N-methylpicolinamide are critical to its application. It is generally described as a white to light yellow or light orange crystalline powder. Its melting point is typically in the range of 110-112°C, a key parameter for quality control. The molecular formula is C13H13N3O2, with a molecular weight of 243.26 g/mol. Its solubility in common organic solvents like DMSO and methanol is usually described as slight, which is important for reaction setup and purification procedures.

The bifunctional nature of the molecule, with both an amino group and an amide group, makes it highly reactive and adaptable for further chemical modifications. The primary amine group on the phenoxy ring and the pyridine ring itself offer multiple sites for derivatization, enabling the construction of diverse molecular architectures. This versatility is precisely why it is sought after as an intermediate in the synthesis of kinase inhibitors and other bioactive compounds relevant to medicinal chemistry.

When procuring 4-(4-Aminophenoxy)-N-methylpicolinamide, understanding these synthesis principles and properties ensures that you can critically evaluate supplier specifications. Knowing the typical synthetic pathway helps in anticipating potential impurities and establishing appropriate quality checks. For researchers and procurement managers, whether you buy 4-(4-Aminophenoxy)-N-methylpicolinamide for R&D purposes or larger-scale manufacturing, confirming these basic chemical attributes from your manufacturer is a crucial step.

In summary, the synthesis of 4-(4-Aminophenoxy)-N-methylpicolinamide is achievable through established organic chemistry routes, yielding a crystalline solid with a defined melting point and characteristic solubility. Its structural features make it an indispensable intermediate for developing novel pharmaceuticals, driving innovation in areas such as targeted cancer therapies. Understanding its properties empowers users to make informed sourcing decisions.