Kato, Tetzuso; Niitsuma, Takuitsu; Kusaka, Noriko published the article 《Reaction of chloropyridine N-oxides with potassium amide in liquid ammonia》. Keywords: AMIDES; AMMONIA; CHEMISTRY, PHARMACEUTICAL; EXPERIMENTAL LAB STUDY; POTASSIUM; PYRIDINES.They researched the compound: 2-Chloropyridine 1-oxide( cas:2402-95-1 ).Synthetic Route of C5H4ClNO. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:2402-95-1) here.
2-Chloropyridine 1-oxide forms 2-aminopyridine 1-oxide (m. 163-4°) and 3-aminopyridine 1-oxide (m. 119-20°), though in a low yield, on treatment with liquid NH3 in the presence of KNH2. Under the same conditions, 3- and 4-chloropyridine 1-oxides give only the 3- and 4-amino compound (m. 64 and 154-5°, resp.), resp. Thus, the mechanism of these reactions is entirely the reverse of that of chloropyridine reported by Hertog (Pieterse and H., CA 58, 11325a; Martens and H., CA 58, 7902a); that of the 2-chloro compound is a benzyne mechanism and that of the 3- and 4-chloro compounds is an amination by an SN2 mechanism.
In addition to the literature in the link below, there is a lot of literature about this compound(2-Chloropyridine 1-oxide)Synthetic Route of C5H4ClNO, illustrating the importance and wide applicability of this compound(2402-95-1).
Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem