1569-16-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.
To a solution of 2-methyl-1,8-naphthyridine (6.024 g, 41.8 mmol) (from step 1) in anhydrous THF (140 mL) at -40 ¡ãC under nitrogen atmosphere was added a 1.0 M solution of lithium bis(trimethylsilyl)amide in THF (88.0 mL) and the reaction mixture was stirred at -40 ¡ãC for 30 min to give a blood-red solution. After stirring for 30 min at – 40 ¡ãC, neat diethyl carbonate (5.60 mL) was added drop wise to above solution in 5 min and the reaction mixture was warmed up to 0 ¡ãC (ice-bath) and stirred at that temperature for 2 h to give a dark reddish-orange solution. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (60.0 mL) to give an orange-red solution and the THF was removed in vacuo to give an orange-red mixture. The resulting mixture was extracted with ethyl acetate (3¡Á50 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4/MgSO4, filtered and evaporated in vacuo to afford a dark orange-red crystalline solid (8.65 g). The crude residue was purified by Silica-gel flash chromatography using a Varian SF-40-120 g Super Flash silica gel column and elution with 10-100percent ethyl acetate in n-heptane to afford the desired product as a yellow-orange crystalline solid (7.76 g, yield 85percent). LC-MS analysis of the solid shows the desired product’s mass: m/z 217 (M+H) and m/z 239 (M+Na); Calculated for C12H12N2O2: 216.23. 1H NMR (400 MHz, DMSO-d6): delta 1.21 (t, J = 7.0 Hz, 3H), 4.10 (q, 2H), 4.89 (s, 1H), 6.77 (d, J = 9.38 Hz, 1H), 7.14 (m, 1H), 7.46 (d, J = 9.36 Hz, 1H), 7.89 (d, 1H), 8.36 (d, 1H), 11.80 (brs, 1H, -OH). 1H NMR of the isolated product was superimposable with that of an authentic sample of the product.
The chemical industry reduces the impact on the environment during synthesis,1569-16-0,2-Methyl[1,8]-Naphthyridine,I believe this compound will play a more active role in future production and life.
Reference£º
Patent; SAINT LOUIS UNIVERSITY; INDALO THERAPUETICS, INC.; RUMINSKI, Peter, G.; GRIGGS, David, W.; SEIWERT, Scott; (155 pag.)WO2018/132268; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem