Suzuki, Yasuyuki published the artcileReactions of 4-pyridine- and 4-quinolinesulfonic acids with amines, Synthetic Route of 18437-58-6, the publication is Yakugaku Zasshi (1961), 1146-50, database is CAplus.
4-Pyridinesulfonic acid, 4-HO3SC5H4N, (I) (1.6 g.) in 16 ml. 28% NH4OH and a small amount of ZnCl2 in an autoclave heated 2 hrs. at 150-60° cooled, 10 ml. 2N NaOH added, the NH4OH removed and the product extracted with CHCl3 gave 0.65 g. 4H2NC5H4N, m. 157-8°. 2,4-Me(HO3S)C5H3N (3 g.), 30 ml. 28% NH4OH and a small amount ZnCl2 in an autoclave heated 24 hrs. at 150-60° and the product treated as above gave 1.21 g. 2,4-Me(H2N)C5H3N, m. 94-5°. Similarly prepared were the following amino compounds (product, % yield, and m.p. given): 3,4-Me(H2N)C5H3N, 57.2, 107.5-9.0°; 2,6,4-Me2(H2N)C5H2N, 70.8, 192-3°; [from 4-HO3SC9H6N (II)] 4-H2NC9H6N, 79.5, 153°. I (1.6 g.), 10 ml. 33% MeNH2 and a small amount of ZnCl2 heated 24 hrs. at 130° gave 0.87 g. 4-MeNHC5H4N; picrate, m. 122-4°. Similarly, I and Me2NH yielded 72.5% 4-Me2NC5H4N, m. 112-13° (picrate, m. 204°); II and MeNH2 yielded 88.3% 4-MeNHC9H6N, m. 224°; II and Me2NH yielded 76.3% 4-Me2NC9H6N, b10 167° (picrate, m. 192°). 2-HO3SC5H4N (1.6 g.), 3.2 ml. 80% N2H4.H2O, 7 ml. H2O, and a small amount of ZnCl2 in an autoclave heated 24 hrs. at 100-5°, the solution filtered, the filtrate concentrated in vacuo, the residue in 10 ml. 50% KOH extracted with Et2O, and the picrate formed gave 2.1 g. 2-H2NNHC5H4N picrate, m. 162-3° (decomposition). Similarly prepared were the following hydrazine derivatives (starting material, product, % yield and m.p. or m.p. of its salt given): I, 4-H2NNHC5H4N (III), 72, HCl salt, 242-4°; 2-HO3SC9H6N, 2-H2NNHC9H6N, 64.5, picrate, 187-9° (decomposition); II, 4-H2NNHC9H6N (IV), 81.2, HCl salt, 3078°; 2,4-Me(HO3S)C9H5N, 2,4-Me(H2NNH)C9H5N, 73.3, picrate, 206° (decomposition). 4-H2NNHC9H6N.HCl (0.5 g.) in 10 ml. H2O, 2 ml. EtOH and 1 ml. 10% NaOH, while refluxing, treated dropwise with 15 ml. 10% CuSO4, refluxed 1 hr., refluxed 1 hr. with 5 ml. 10% NaOH and the product steam distilled gave 0.25 g. C9H7N; picrate, m. 202-3°. III.HCl (1 g.) in 50 ml. absolute EtOH treated with EtONa (0.16 g. Na and 7 ml. EtOH), the NaCl removed, the solution concentrated to 10 ml., refluxed 1 hr. with 0.8 g. Et pyruvate and the product concentrated gave 1.05 g. Et pyruvate 4-pyridylhydrazone, columns, m. 128-30°. III.HCl (1.45 g.) in 40 ml. MeOH treated with 1 g. KSCN in 10 ml. MeOH, refluxed 9 hrs. and the product concentrated gave 1.4 g. III.HSCN, m. 1079°. III (from 1.6 g. III.HCl) in 10 ml. C5H5N at 0° treated dropwise with 1.55 g. BzCl, stirred 1 hr. at room temperature, kept overnight, the solvent removed, and the residue washed with H2O gave 1.2 g. 4-pyridyldibenzoylhydrazine, m. 2345° (EtOH). III (from 1.45 g. III.HCl) in 10 ml. EtOH and 1 g. AcCH2COMe refluxed 1 hr., the EtOH removed, the residue in 5 ml. 10% NaOH and 10 ml. H2O extracted with CHCl3 and the product distilled gave 1.15 g. 1-(4-pyridyl)3,5-dimethylpyrazole, b5 131-4°; picrate m. 237° (decomposition). A solution of 1.26 g. AcONa.3H2O, 3 ml. H2O, 1 g. IV.HCl, 0.37 g. Me2CO and 1 ml. AcOH refluxed 1.5 hrs., cooled, 4 ml. H2O added and the mixture made alk. with NH4OH and kept overnight at 0° gave 0.62 g. acetone 4-quinolylhydrazone, m. 122°. IV (0.5 g.) in 5 ml. EtOH and 0.34 g. PhCHO refluxed 1 hr. and the product concentrated gave 0.46 g. benzaldehyde 4-quinolylhydrazone, m. 11314°. IV.HCl (0.9 g.) in 20 ml. H2O, 0.63 g. AcONa.3H2O and 0.4 g. pyruvic acid mixed well and the product filtered off gave 0.73 g. pyruvic acid 4-quinolylhydrazone, m. 246° (decomposition). IV (0.35 g.) in 4 ml. EtOH and 0.25 g. Et pyruvate refluxed 1 hr. and the solution concentrated gave 0.31 g. Et pyruvate 4-quinolylhydrazone, m. 178°. IV.HCl (1.4 g.), 0.7 g. KSCN, and 50 ml. MeOH refluxed 12 hrs. and the solution concentrated gave 1.2 g. IV.HSCN, m. 168-9°. IV (0.5 g.) in 5 ml. C5-H5N and 0.44 g. BzCl refluxed 3 hrs. and the product concentrated gave 0.37 g. 1-(4-quinolyl)-2-(benzoyl)hydrazine, m. 129.5-30.5°. IV (0.66 g.) in 5 ml. EtOH and 0.42 g. AcCH2COMe refluxed 1 hr., the EtOH removed and the residue in 10% NaOH extracted with CHCl3 gave 0.66 g. 1-(4quinolyl)-3,5-dimethylpyrrazole, b4 180-1°; picrate m. 198° (MeOH).
Yakugaku Zasshi published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C11H9ClN2O, Synthetic Route of 18437-58-6.
Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem