Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Roczniki Chemii called Investigations on the isomerization of ring-substituted derivatives of 3-nitraminopyridines. I. Chloro-3-nitraminopyridines, Author is Czuba, Wladyslaw, which mentions a compound: 22353-34-0, SMILESS is NC1=CC(=CN=C1)Cl, Molecular C5H5ClN2, Category: dioxole.
6-(m. 139°), 2- (m. 100-3°), 5- (m. 146°), and 4-Chloro-3-nitraminopyridine (m. 179°) (all with decomposition) heated to 40° in concentrated H2SO4 underwent isomerization to 6,6′-dichloro- (I) (m. 215-17°, yield 10%) and 6,6′-dichloro-2-nitro- (II) (m. 165°, 9%), 2,2′-dichloro- (III) (m. 237-9°, 26%), 5,5′-dichloro- 3, 3′-azopyridine (IV) (m. 183°, 16%) and 5-chloro-3-hydroxypyridine (m. 158°, 32%), and 4,4′-dichloro-3,3′-azopyridine (V) (m. 164°, 40%), resp. I, III, IV, and V with SnCl2, Sn, or NaSH gave the hydrazopyridines, m. 183-5°, 209°, 128-31°, and 172°, resp., yields 70-91%. Reduction of III yielded 6-chloro-2,3-diamino- and -3-aminopyridine. A new method of preparation of 3-amino-5-chloropyridine (VI) was described. Br (32 g.) dissolved in 25 g. NaOH, 50 ml. H2O, and 250 g. ice, 25.5 g. 5-chloronicotinic acid amide added, the mixture heated 0.5 hr. at 75°, the solution saturated with NaCl, extracted with Et2O, dried (K2CO3), and evaporated gave 83% VI, m. 82° (C6H6 + ligroine).
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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem