Substituted 2-picolines derived from 6-amino-2-picoline was written by Parker, Edwin D.;Shive, Wm.. And the article was included in Journal of the American Chemical Society in 1947.Recommanded Product: 218770-02-6 This article mentions the following:
6-Amino-2-picoline (Zeide, C.A. 18, 1497) on nitration and rearrangement, with steam distillation, yields 58.4% 6-amino-3-nitro-2-picoline (I) and 25.3% 5-NO2 isomer (II). II (1.56 g.), 0.77 g. NaNO2, and 20 cc. concentrated HCl, allowed to stand in a sealed tube at 0° several hrs. and then heated at 80° 2 hrs., give 38% 6-chloro-5-nitro-2-picoline (III), pale yellow, m. 70-70.8° (separated by steam distillation), and 25-30% 6-hydroxy-5-nitro-2-picoline, m. 226-7° (decomposition). Catalytic reduction of III in EtOAc-EtOH with Pt oxide and Pd-BaSO4 at room temperature gives 60% 5-amino-2-picoline (IV), m. 95-6.5° (Graf, C. A. 26, 1932); the diazo reaction gives 5-hydroxy-2-picoline, m. 166-7° (the β-hydroxy-α-picoline of Wulff, U.S. 1,880,645, C.A. 27, 513). Catalytic reduction of II in EtOAc-EtOH over Pt oxide at room temperature gives 65% 5-amino-6-chloro-2-picoline (V), m. 82-3°, and 20% IV; reduction of II with SnCl2 in concentrated HCl gives 83% V. V (0.40 g.) in 75 cc. N H2SO4, treated slowly with 0.2 g. NaNO2 in 10 cc. H2O and the diazo solution heated, gives 40 mg. 6-chloro-5-hydroxy-2-picoline, m. 196-8°. I (0.92 g.) in 10 cc. concentrated HCl with 0.47 g. NaNO2 gives 29% 6-chloro-3-nitro-2-picoline (VI), pale yellow, m. 54-5°, and 49% 6-hydroxy-3-nitro-2-picoline, light yellow, m. 234-6°. Reduction of 0.56 g. VI in 6 cc. concentrated HCl with 2.5 g. SnCl4 gives 91% 3-amino-6-chloro-2-picoline (VIA), m. 93-4°; diazotization of 0.32 g. in 85 cc. N H2SO4 gives 22% 6-chloro-3-hydroxy-2-picoline, m. 208°. I with Cl in AcOH, allowed to stand overnight, gives 50% 3-amino-5-chloro-3-nitro-2-picoline, light yellow, m. 215.4-16°; 5-Br derivative (VII), yellow, m. 211.6-12.4°; in 1 experiment there resulted the perbromide of I which, with concentrated H2SO4, gives the Br derivative VII (2.112 g.), and 0.697 g. NaNO2 in 15 cc. concentrated HCl give 32.1% 5-bromo-6-chloro-3-nitro-2-picoline (VIII), light yellow, m. 93°, and 26.8% of the 6-HO derivative, light yellow, m. 261° (decomposition). Reduction of VIII with SnCl2 in concentrated HCl gives 96.4% 3-amino-5-bromo-6-chloro-2-picoline (IX), m. 162.5-4°. Catalytic reduction of IX in EtOH over Pd-C gives 38% unchanged IX and 39% 3-amino-2-picoline (X); reduction of VIA likewise gives 37% X. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-methylpyridin-3-ol (cas: 218770-02-6Recommanded Product: 218770-02-6).
6-Chloro-2-methylpyridin-3-ol (cas: 218770-02-6) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Recommanded Product: 218770-02-6