Nakashima, Tatsumi et al. published their research in Yakugaku Zasshi in 1957 | CAS: 4783-68-0

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Computed Properties of C11H9NO

Oximes of 2-acylpyridine and 2-acylquinoline was written by Nakashima, Tatsumi. And the article was included in Yakugaku Zasshi in 1957.Computed Properties of C11H9NO This article mentions the following:

2-NCC5H4N reacted with RMgX in Et2O to give 2-ROCC5H4N (I) and the I reacted with NH2OH.HCl to give the oxime. I prepared were (R. b.p./mm. and m.p. of its oxime given): Me, 65-6°/8, 121°; Et, 80-4°/5, 106°; PhCH2, 138-42°/2, 157° [picrate, C19H14O8N4, m. 161° (decomposition); phenylhydrazone, C19H17N3, m. 96°]; Ph, 165°/7, 152°. 2-MeC5H4N (30 g.) was transformed into 2-PhCH:CHC5H4N, then 2-PhCHBrCHBrC5H4N, which with alc. KOH yielded 30 g. 2-PhCCC5H4N (II), b5 174°, m. 78-80°. II with H2SO4 kept 48 hrs. at room temperature, the product treated with NH4OH to pH 8, and extracted with Et2O gave 2-PhCOCH2C5H4N (III), m. 54°, with poor yield; oxime, m. 120°. Alternatively, treating 2-MeC5H4N with Li to form 2-LiCH2C5H4N, and treating this with BzOMe yielded 75% III. Similarly are prepared 2-RCOC9H6N (IV) (R, m.p. and m.p. of oxime given): Me, 52-3°, 143.5°; Et, 59-60°, 107°; Ph, 111°, 168-9°. 2-EtO2CC9H6N and PhCH2CN in EtOH with EtONa yielded 2-PhCH(CN)COC9H6N (V), m. 100°. V (1 g.), 1 g. AcOH, 0.7 g. H2SO4, and 1.5 ml. H2O heated at 90-100°, and 1 hr. at 120°, the product poured in ice H2O, and recrystallized from EtOH gave 0.85 g. 2-PhCH2COC9H6N, m. 78° (oxime, m. 128.5°). 2-PhCCC9H6N (19 g.) and 225 ml. H2SO4 treated as in III gave 1.5 g. 2-PhCOCH2C9H6N (VI), m. 120-2° (oxime, m. 174-5°). Alternatively, a solution of 1.4 g. Li in 120 ml. Et2O and 16 g. PhBr treated with 14.5 g. 2-MeC9H6N in Et2O and 7.4 g. BzOMe, the product poured in 60 g. ice and 8 g. NH4Cl, and the Et2O removed gave 4.7 g. VI, m. 122°. 2-PhC(:NOH)C9H6N in 10 ml. CHCl3 treated with 0.66 g. SOCl2, the CHCl3 and SOCl2 removed in vacuo, the residue refluxed 3 hrs. with 6N HCl, the product extracted with Et2O gave 0.5 g. BzOH, m. 119-21°; the HCl layer made alk. and extracted with Et2O gave 0.4 g. 2-H2NC9H6N, m. 128°. 2-PhC(:NOH)C6H4N and 2-acylquinolines do not form complex salt with Fe++. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Computed Properties of C11H9NO).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Computed Properties of C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem