Diazotization and diazo reactions of 2-aminopyridine was written by Chichibabin, A. E.. And the article was included in J. Russ. Phys.-Chem. Soc. in 1920.Synthetic Route of C11H9NO This article mentions the following:
Attempts made to introduce the C5H5N nucleus into organic compounds by the Grignard reaction on 2-bromo- and 2-iodopyridine failed; the preparation of these substances from Na 2-pyridineisodiazoxide (C. A. 10, 2898) has been improved and is described. Successful results are, however, obtained by the interaction of the latter substance with phenol. After removing phenol, etc., 3 substances are obtained, one of which may be readily separated owing to its insolubility in alkali hydroxides. This consists of 2-phenoxypyridine, b. 277-.5°, m. 46-8°, possessing an odor reminiscent of Ph2O; the orange chloroplatinate, m. 175-7°, and the picrate were also prepared The 2 compounds soluble in alkali are isomeric pyridylphenols, and may be separated by crystallization from C6H6. The less soluble compound seps. in white leaflets or thick, lustrous, hexagonal plates containing a mol. of C6H6 of crystallization; after removing the latter it m. 159-60° and is readily soluble both in dilute acids and alkalies, being precipitated from the latter by CO2. It is probably p-2-pyridylphenol. The HCl salt, m. 215-8°; the chloroplatinate, orange-yellow, m. 210-1.5° (decomposition), while the sparingly soluble picrate, m. 202-3°. The 2nd, more soluble pyridylphenol is probably o-2-pyridylphenol, and is obtained in large, greenish yellow prisms, m. 56°; it is less soluble in alc. than the preceding compound and its phenolic properties are less marked; the yellow color may perhaps be due to a quinonoid structure. The HCl salt is obtained in a hydrated form, colorless prisms, m. 56°, which lose water in a desiccator, the anhydrous substance m. 167-70°. The chloroplatinate, softens at 227-8°. The picrate, yellow, m. 174°. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Synthetic Route of C11H9NO).
2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Synthetic Route of C11H9NO