2,5-PYRIDINEDICARBOXYLICACIDDIETHYLESTER

Concentrated sulfuric acid (3.9 mL, 71.6 mmol) was added dropwise over 15 minutes to a stirred suspension of 2, 5-pyridinedicarboxylic acid (3.0 g, 17.9 mol) in absolute ethanol (10 mL) and the resulting mixture heated to reflux for 18 hours. The solution was allowed to cool to room temperature and the solvents evaporated under reduced pressure. Saturated NaHCC>3 solution was added to the residue to adjust the pH to -8 then the aqueous phase was extracted with EtOAc (4 x 50 mL). The combined organic extracts were washed with brine (30 mL), dried (Na2S0Diethyl pyridine-2, 5-dicarboxylate (5.3)Pyridine-2, 5-dicarboxylic acid (20.0 g, 120 mmol) was dissolved in ethanol (200 mL) and treated with concentrated solution of sulfuric acid (2.0 mL, 36 mmol) in ethanol (20 mL). The reaction was heated under reflux for 4hrs, concentrated and dissolved in EtOAc (10 mL). The mixture was washed with water (50mL), brine (50 mL), dried over sodium sulfate, filtered and evapourated to afford diethyl pyridine-2, 5-dicarboxylate (18 g, 67 percent). 1 H NMR (400MHz CDCI(0201) 2, 5-pyridinedicarboxylic acid (25.08 g; 150 mmol) was added to ethanol (1, 800 mL). Aqueous sulfuric acid (1.32 g) was added. The mixture was heated at reflux (about 78° C.) for 58 hours, during which time water was removed from the reaction. The reaction progress was monitored using NMR spectroscopy. After the 2, 5-diethyl-2, 5-pyridinedicarboxylate had been formed in >97percent purity by NMR, the reaction mixture was allowed to cool to ambient temperature and was extracted with 2-methyltetrahydrofuran. The combined organic layers were washed with a saturated aqueous brine solution and deionised water, and dried (MgSO

Molecular Weight:223.22
XLogP3:1.6
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:223.08445790
Monoisotopic Mass:223.08445790
Topological Polar Surface Area:65.5
Heavy Atom Count:16
Complexity:254
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes