The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《4,6-Dichloro- and 4,5,6-trichloropicolinic acid》. Authors are Graf, Roderich.The article about the compound:3-Chloropicolinamidecas:114080-95-4,SMILESS:O=C(N)C1=NC=CC=C1Cl).Related Products of 114080-95-4. Through the article, more information about this compound (cas:114080-95-4) is conveyed.
cf. C. A. 25, 2428. Picolinic acid-HCl (200 g.) and 350 cc. SOCl2, gently boiled 10 days, give 30 g. mono-Cl acid, 100 g. di-Cl acid and 30 g. of a mixture of the di- and tri-Cl acids. That the di-Cl acid is the 4,6-Cl2 derivative is shown by the following reactions: The acid chloride and N2H4.H2O in C6H6 give sec-bis(4,6-dichloropicolinic acid) hydrazide, m. above 300°; the Me ester gives 4,6-dichloropicolinic acid hydrazide, m. 154° (benzal derivative, m. 165°); the azide m. 74° and with absolute EtOH yields 4,6-di-chloro-2-carbethoxypyridine, m. 75°; dilute AcOH gives the 2-NH2 derivative (I), m. 108°; with HI I yields a compound, m. 137°, which may be the 6-iodo-4-chloro derivative The Ac derivative of I n. 218-9°. The diazo solution from I in H2SO4 gives 4,6-dichloro-2-hydroxy-pyridine, m. 151°, and in concentrated HCl gives 2,4,6-trichloropyridine, m. 33°; this also results from 2,6-dichloro-4-aminopyridine. Heating the 4,6-Cl2 acid with 80% H2SO4 8 hrs. gives 4-chloro-6-hydroxypicolinic acid (Seyfferth, J. Chem. Soc. 67, 408(1895). 4,5,6-Trichloropicolinic acid (II), crystallizing with 1 mol. H2O, m. 123°, is obtained pure by distillation of the chloride and then of the Me ester, m. 125°; II and HI with some red P, heated 8 hrs. at 150°, give 5-chloropicolinic acid, m. 170°. The amide of II m. 169°; the Ph ester m. 138°. Heating the Me ester with HI and red P 5 hrs. gives 4-iodo-5-chloropicolinic acid, m. 159° (decomposition); refluxed with SOCl2 for 4 hrs., the I is replaced by Cl, giving 4,5-dichloropicolinic acid, crystals with 1 mol. H2O, m. 179-80° (Ost, J. prakt. Chem. 27, 274(1882)). Refluxing the Me ester with 80% H2SO4 4 hrs. gives 4,5-dichloro-6-hydroxypicolinic acid, crystallizing with 1 mol. H2O, m. 284° (decomposition). 3-Chloropicolinic acid, m. 121°; amide, m. 140°.
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