As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO452,mainly used in chemical industry, its synthesis route is as follows.,249889-68-7
The residue was suspended in diisopropylethylamine (7 ml), phosphorus oxychloride (1.5 ml) was added to the suspension, and the mixture was stirred at 100C for one hr. Water was added to the reaction mixture under ice cooling. The aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-chloroform system to give 8-chloro-2-methoxy-[1,5]naphthyridine (572 mg, yield 29%) (3 steps). 8-Chloro-2-methoxy-[1,5]naphthyridine (50 mg), 5,6-dimethyl-[2,2′]bipyridinyl-3-ol (51 mg), and 4-dimethylaminopyridine (94 mg) were dissolved in dimethylsulfoxide (1.5 ml), cesium carbonate (251 mg) was added to the solution, and the mixture was stirred at 130C overnight. The reaction mixture was cooled to room temperature, and water was added thereto. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (70 mg, yield 75%). 1H-NMR (CDCl3, 400 MHz): delta 2.34 (s, 3H), 2.66 (s, 3H), 3.92 (s, 3H), 6.92 (d, J = 5.4 Hz, 1H), 7.17 – 7.26 (m, 3H), 7.65 (dd, J = 7.6, 7.6 Hz, 1H), 8.16 (d, J = 8.1 Hz, 1H), 8.36 (s, 1H), 8.53 (d, J = 5.9 Hz, 1H), 8.58 (m, 1H) Mass spectrometric value (ESI-MS, m/z): 381 (M+Na)+
With the synthetic route has been constantly updated, we look forward to future research findings about 8-Chloro-2-methoxy-1,5-naphthyridine,belong naphthyridine compound
Reference£º
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem