Reference of 142896-15-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 142896-15-9, name is Methyl 2,6-dimethylisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.
A mixture of 1.372 g (8.3 mmol) of (3), 60 mg of AlBN and 2.866 g (16.1 mmol) of NBS in 120 ml of CCl4 is refluxed under a nitrogen atmosphere and under irradiation with a 100 W lamp, for 8 hours. The reaction medium is then returned to room temperature, after which it is washed with 200 ml of saturated NaHCO3 solution. After removing the lower phase (CCl4), the aqueous phase is extracted 4 times with 50 ml of CHCl3; the combined organic extracts are then washed with 100 ml of H2O, dried (Na2SO4) and then concentrated to dryness. Purification of the residue obtained by chromatography on silica [gradient: cyclohexane-CH2Cl2 (80/20) to pure CH2Cl2) makes it possible to separate out a first fraction of the bromo derivative (4), from the polybromo species, from a mixture of isomers of symmetrical and asymmetrical dibromo derivatives and from the monobromo species also formed. [0153] In order to have available a larger amount of methyl 2,6-dibromomethyl isonicotinate, the monobromo compound isolated above [0.543 g (2.2 mmol)] is mixed with 0.4 g (2.2 mmol) of NBS, 23 mg of AIBN and 50 ml of CCl4 and is then treated under the above bromination conditions to give a second fraction of (4). [0154] Finally, a purification by chromatography on silica [gradient: pure cyclohexane to cyclohexane/EtOAc (85/15)] of the mixtures of dibromoisomers, isolated in the above two reactions, gives a final fraction of (4), i.e. 596 mg in total (22%). [0155] m.p.: 90-92 C. [0156] TLC: Rf: 0.6 (SiO2/CH2Cl2) [0157] HPLC: Tr: 20 min 5 sec [0158] UV: CHCl3: 290.8 nm (4270); 240.3 nm (3010) [0159] NMR: 1H CDCl3; internal reference TMS [0160] 3.98 (s, 3H, CH3); 4.58 (s, 4H, CH2); 7.92 (s, 2H, Py) [0161] 13C CDCl3; internal reference 77.0 ppm [0162] 32.8 (CH2); 52.9 (OCH3); 122.2 (Ct); 139.8, 157.9 (Cq); [0163] 164.7 (CO). [0164] MS (EI): 322.9 (M+, 15); 243.9 (M+-Br, 100); 163 (M+-2Br, 15.7). [0165] MA: C9H9NO2Br2 (322.98) [0166] Calculated: C 33.47H 2.80 N 4.33 O 9.90 [0167] Found: C 33.69H 2.81 N 4.29 O 10.17
According to the analysis of related databases, 142896-15-9, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Autiero, Herve; Bazin, Herve; Mathis, Gerard; US2004/92726; (2004); A1;,
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