With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4488-22-6,[1,1′-Binaphthalene]-2,2′-diamine,as a common compound, the synthetic route is as follows.
Racemic 1,1?-binaphthalenyl-2,2?-diamine (2.84 g, 10 mmol) was dissolved in freshly distilled No.7 acetonitrile (60 mL), then No.8 potassium carbonate (13.82 g, 100 mmol) and No.9 potassium iodide (1.33 g, 8.0 mmol) were added. The reaction mixture was heated to reflux under nitrogen atmosphere. Then No.10 ethyl bromoacetate (8.35 g, 50 mmol) was added dropwise and the reaction mixture was refluxed for 72 h. The mixture was then cooled, diluted with water (200 mL) and extracted with ethyl acetate (3 ¡Á 60 mL). The combined organic layer was washed with water (60 mL), dried with MgSO4, and then filtered and evaporated under reduced pressure to remove the solvent. The residue was purified by flash chromatography on silica using No.11 ethyl acetate-petroleum ether (v/v 1:6) as eluent to give light yellow No.12 solid. (yield 54%): 1H NMR (500 MHz, DMSO-d6): 7.86-7.90 (m, 4H), 6.90-7.34 (m, 8H), 3.68-3.85 (m, 16H), 1.02 (t, 12H, J = 7.1 Hz). (0006) A mixture of above resulted solid product (3.15 g, 5 mmol), ethanol (50 mL) and 2 M aqueous solution of NaOH (8 mL) was refluxed under nitrogen atmosphere for 24 h. The solution was then evaporated to remove most solvent, and then cooled in ice-water, 3 M hydrochloric acid was added until pH 3-4. The crude product was extracted with ethyl acetate (2 ¡Á 60 mL). The organic layers were combined and washed with brine (80 mL), dried with Na2SO4, and filtered. The solvent was then removed under reduced pressure. The residue was purified by flash chromatography on silica using ethyl acetate as eluent, from which a yellowish solid of H4L ligand was collected in 76% yield. Mp: 172-173 C; 1H NMR (500 MHz, DMSO-d6) 7.91 (d, 2H, J = 9.0 Hz), 7.86 (d, 2H, J = 8.0 Hz), 7.42 (d, 2H, J = 8.0 Hz), 7.31 (t, 2H, J = 8.0 Hz); 7.19 (t, 2H, J = 8.0 Hz); 6.88 (d, 2H, J = 8.6 Hz); 3.66 (s, 8H); 13C NMR (125.77 MHz, DMSO-d6):172.67, 147.89, 134.27, 130.18, 128.89, 128.38, 126.85, 125.10, 124.47, 124.16, 123.24, 53.13; IR (KBr, cm-1), 3418 (w), 3056 (w), 2929 (m), 1719 (s), 1619 (m), 1594 (m), 1507 (s), 1407 (w), 1375 (w), 1211 (s), 969 (s), 816 (s), 750 (s); Anal. Calc. for C28H24N2O8: C, 65.11; H, 4.68; N, 5.42. Found: C, 65.29; H, 4.53; N, 5.36%., 4488-22-6
Big data shows that 4488-22-6 is playing an increasingly important role.
Reference£º
Article; Huang, Wan-Yun; Chen, Zi-Lu; Zou, Hua-Hong; Liu, Dong-Cheng; Liang, Fu-Pei; Polyhedron; vol. 50; 1; (2013); p. 1 – 9;,
Chiral Catalysts
Chiral catalysts – SlideShare