New learning discoveries about [1,1′-Biphenyl]-2-carbonitrile

The synthetic route of 24973-49-7 has been constantly updated, and we look forward to future research findings.

24973-49-7, name is [1,1′-Biphenyl]-2-carbonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: nitriles-buliding-blocks

General procedure: A stirring suspension of lithium aluminum hydride (1.1equiv) in anhydrous THF was treated dropwise under N2 with a solution of aluminum chloride (0.9equiv) in THF. The reaction mixture was maintained at room temperature during the addition by means of a water bath. After addition was complete, the reaction mixture was stirred vigorously for 20min and then cooled to 0C before adding dropwise a solution of biphenyl-2-carbonitrile 4 (1.0equiv) in THF. After complete addition, stirring was continued for 2h and the reaction was quenched by slowly adding methanol followed by water. The mixture was concentrated under reduced pressure, and the residue was extracted with 1N HCl. The aqueous phase were combined, washed with EtOAc and neutralized by addition of 10N NaOH. The mixture was extracted with CH2Cl2, the organic phase was combined, washed with water, dried over Na2SO4 and evaporated under reduced pressure. The residue was filtered through a pad of silica gel, and the filtrate was evaporated and dried to give the product 5 in 60-75% yields. 4.3.1 Biphenyl-2-ylmethanamine (5-1) The reaction of lithium aluminum hydride (2.15 ml, 2.15 mmol) in anhydrous THF, aluminum chloride (234 mg, 1.76 mmol), and biphenyl-2-carbonitrile (350 mg, 1.95 mmol) in THF (5 ml) gave the title compound 5-1 (256 mg, 1.40 mmol, 72% yield). 1H NMR (400 MHz, CDCl3) delta 7.46 (d, J = 7.5 Hz, 1H), 7.41-7.40 (m, 2H), 7.37-7.32 (m, 3H), 7.30 (td, J = 7.5, 1.3 Hz, 1H), 7.24 (dd, J = 8.1, 2.1 Hz, 1H), 3.81 (s, 2H), 1.34 (s, 2H).

The synthetic route of 24973-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, Youngjae; Tae, Jinsung; Lee, Kangho; Rhim, Hyewhon; Choo, Il Han; Cho, Heeyeong; Park, Woo-Kyu; Keum, Gyochang; Choo, Hyunah; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4587 – 4596;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts