Profft, E.’s team published research in Journal fuer Praktische Chemie (Leipzig) in 9 | CAS: 18437-58-6

Journal fuer Praktische Chemie (Leipzig) 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 C6H8N2, SDS of cas: 18437-58-6.

Profft, E. published the artcileThe preparation of 4-halo-2-methylpyridines, SDS of cas: 18437-58-6, the publication is Journal fuer Praktische Chemie (Leipzig) (1959), 164-72, database is CAplus.

Diazotization of 2-methyl-4-aminopyridine (I) (Boekelheide, C.A. 49, 5256f) with HBr and NaNO2 at -15°, decomposition of the diazonium salt by bringing slowly to room temperature, addition of aqueous NaOH, and steam distillation gave 72% 2-methyl-4-bromopyridine (II), b. 184°, b1474-6°, n20D 1.5542. II treated with MeI in C6H6 10 hrs. at room temperature gave the methiodide, m. 214° (decomposition); II picrate m. 186°. II, AcOH, and H2O2 gave 55% 2-methyl-4-bromopyridine N-oxide (III), b14 178°, also prepared from 2-methyl-4-nitropyridine N-oxide and HBr in an autoclave at 160° (Suzuki, C.A. 47, 8074b). III was reduced to II by powd. Fe in AcOH at 100°. II.HCl and Reinecke salt in H2O gave on standing II reineckate, m. 152-3°. From I, dilute H2SO4, and NaNO2 at -15°, followed by addition of cold aqueous KI, warming to room temperature, addition of NaOH, and extraction with Et2O was obtained 52% 2-methyl-4-iodopyridine (IV), b14 84-6°, m. 42°; picrate, yellow, decomposed 209°; reineckate m. 156-7°; methiodide m. 238° (decomposition). IV, AcOH, and H2O2 gave 2-methyl-4-iodopyridine N-oxide, b14 192-4°. I with HBF4 and NaNO2 at -15° followed by warming, NaOH addition, and steam distillation gave 43% 2-methyl-4-fluoropyridine (V), b. 128-32°, n20D 1.4713, more easily soluble in H2O than the Br and iodo analogs; V picrate m. 152°; reineckate m. 158-9°; methiodide m. 191°; N-oxide (made by both methods shown for III) b14 136-8°. IV (5 g.) refluxed at 210° with 10 g. powd. Cu gave a solid mass, which ground in a mortar, extracted with 2N HCl, the solution neutralized with NaOH, extracted with Et2O, and the extract evaporated gave 52% 2,2′-dimethyl-4,4′-bipyridyl, yellowish, m. 83°; picrate, yellow, decompose 237°.

Journal fuer Praktische Chemie (Leipzig) 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 C6H8N2, SDS of cas: 18437-58-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem