2,6-Pyridinedicarboxaldehyde

White to gray solid

A solution of 2, 6-bis(1-pyrrolidinylcarbonyl)pyridine (3.0 g, 11 mmol) in anhydrous THF (20 mL) was added dropwise at 0 °C to a well-stirred solution of LiAlH4 (0.31 g, 8.24 mmol; prepared in 30 mL of dry THF by stirring within 16 h). After 40 min, the reaction mixture was carefully hydrolyzed with 2M aq. HCl. The organic phase was separated, and the aqueous phase was extracted with CH2Cl2 (5×10 mL). Combined organic phase was dried over Na2SO4. Removal of the solvent in vacuo and recrystallization from diethyl ether furnished the product as an almost colorless powder. The yield was 1.30 g (76percent).LiAlH4 (7 mmol) was stirred for 16 h in THF (30 ml) at 20 °C. After cooling to 0 °C, 2, 6-pyridine dicarboxamide (10 mmol) in THF (20 ml) was added. After 1 h of stirring (monitored by TLC) the mixture was hydrolysed with 2 M aq. HCl and extracted with CH2Cl2 (5 x 10 ml). After evaporation of the solvent, the residue was purified by crystallization or flash chromatography (silica gel 40, CHCl3).300 mg (2.17 mmol) of the compound prepared in the above step 2) was dissolved in 50 ml of 1, 4-dioxane, 2.6 g (23.8 mmol) of selenium dioxide was added, and the mixture was refluxed with stirring for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered through a celite-filled filter to remove selenium dioxide. The obtained filtrate was distilled under reduced pressure and dried under reduced pressure to give the title compound (300 mg, 99percent).A mixture of pyridine-2, 6-dimethanol (10.00 g, 71.86 mmol) and Dess-Martin periodinane (67.06 g, 158.10 mmol) were suspended in 400 mL of dichloromethane. The reaction mixture was stirred at room temperature for 12 hours. Subsequently, 100 mL of water was added to the reaction and the mixture was stirred at room temperature for an additional 12 hours. A 300 mL 50/50 mixture of saturated NaHCO3 and 10percent NaTake a 100 ml round bottom flask and add 1.5 g (10.8 mmol) of 2, 6-pyridine dimethanol, 2.4 g (21.8mmol) of SeO1.0 g (7.2 mmol) of compound 4, 1.60 g (14.4 mmol) of SeO 2, 30 mL of 1, 4-dioxane was added to a 50 mL single-necked round bottom flask 1 and subjected to electromagnetic stirring at 101 ° C for 5 h to obtain a compound 2 reaction product.The reaction product containing the compound 2 obtained in the step (1) was filtered to remove the black solid, and the filtrate was distilled under reduced pressure to remove the solvent 1, 4-dioxane to obtain the crude product. The resulting crude product was separated by column chromatography using 500 mL of acetic acid Ethyl ester and petroleum ether, wherein the volume ratio of ethyl acetate to petroleum ether in the mixture is 1: 3 to obtain the compound 2, the mass of the compound 2 being 0.675 g , The yield was 69.39percent;The new-made MnOGeneral procedure: In a representative procedure, to a solution of acid chloride such as 4-BrC

Molecular Weight:135.12
XLogP3:0.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:135.032028402
Monoisotopic Mass:135.032028402
Topological Polar Surface Area:47
Heavy Atom Count:10
Complexity:122
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes