2 2'-BIPYRIDINE-4 4'-DICARBOXALDEHYDE

General procedure: To a 100ml two-necked RB, dimethyl bipyridine 1 (500 mg, 0.00271 mol, 1.0 equiv.)was taken, added 100 mL of 1, 4-dioxane drop wise and stirred to get a homogenous mixtureand the solution was purged with nitrogen for 15 min bubbling nitrogen into the dioxane withstirring. 0. 663 mg of SeO2 (2.2 equiv) was added and refluxed under N2 atmosphere for 44hours. After the completion of the reaction (Monitored by TLC), the reaction mixture waswashed with warm 1, 4-dioxane for 2 to 3 minutes and filtered and 1, 4-dioxane was removedunder reduced pressure. The residue was then dissolved in hot distilled ethyl acetate, filteredand again washed with hot ethyl acetate. The ethyl acetate layer was washed with 1MNa2CO3 (250ml) to remove additional carboxylic acid. The organic layer was dried withanhydrous Na2SO4 and concentrated and the residue was purified on alumina using 60percent ethylacetate in petroleum ether to afford the newly synthesized 2, 2'-bipyridine 4, 4'-dicarbaldehyde was thoroughly characterized by spectroscopic technique such as IR, 1HNMR, 13C NMR and HRMS.7 was synthesized before by applying other methodologies.22, 23 0.9 g of 6 (2.9 mmol) were dissolved in 25 cm3anhydrous diethyl ether and 25 cm3 anhydrous toluene undera nitrogen atmosphere at -78 °C. Butyl lithium in hexane (5cm3, 2.5 mol/L)was added dropwise. The solutionwas stirredat -78 °C for 90 min before 8.0 cm3 anhydrous dimethyl formamidewere added. The resulting solution was then stirredfor another 90 min at the same temperature. To stop the reaction50 cm3 2 N hydrochloric acid were added at -78° C andthe solution was then allowed to reach room temperature. Theorganic phase was separated and the aqueous phase was neutralizedwith diluted sodium hydroxide solution. A smooth white precipitate formed that was three times extracted withCH2Cl2. The solvent was evaporated under reduced pressureand a pale brown oil that solidified to a pale brown solid wasobtained. Yield: 35percent (0.215 g, 1.01 mmol); M.p.: 194–196°C, literature 192 °C.24

Molecular Weight:212.20
XLogP3:0.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:212.058577502
Monoisotopic Mass:212.058577502
Topological Polar Surface Area:59.9
Heavy Atom Count:16
Complexity:231
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes