2,6-Dichloro-3-pyridinecarboxaldehyde

To a solution of (2, 6-dichloropyridin-3-yl)methanol (1.0 g, 5.62 mmol) in CHDissolve (2, 6-dichloropyridin-3-yl)-methanol (876 mg, 4.92 mmol) in dichloromethane (20.mL). Add pyridium chlorochromate (2.12 g, 9.84 mmol). Stir for 2 hours. Add diethyl ether and stir for 20 minutes. Filter the mixture through a pad of Celite.(R). and silica gel and concentrate to give 2, 6-dichloropyridine-3-carbaldehyde (575 mg, 66percent): Lithium diisopropylamide (2 M, 20.5 mL, 40.53 mmol, 1.2 eq.) was added into anhydrous tetrahydrofuran (20 mL) at -78 °C. Compound 1-1 (5.0 g, 33.78 mmol, 1.0 eq.) in tetrahydrofuran (20 mL) was added dropwise over 1 h at -78 °C. NN-Dimethylformamide (7.5 g, 101.35 mmol, 3.0 eq.) was added into the solution, and the mixture was stirred for another 2 hat -78 °C. Saturated ammonium chloride (60 mL) was added to the mixture to quench the reaction. The solution was evaporated to remove tetrahydrofuran and extracted with ethyl acetate (3 x 50 mL). The organic layer was collected, dried over sodium sulfate, and evaporated to give the crude product, which was purified by silica gel column chromatography (100percent petroleum ether to ethyl acetate : petroleum ether = 1:10) to give compound 1-2 as a white solid (3.5 g, yield: 59percent). MS (ESI) m/z 176.0 [M+H]Under NBuLi (2.5 M in hexanes, 36 mL, 90 mmol) was slowly added to diisopropylamine (12.5 mL, 89.2 mmol) in THF (80 mL) at O13(3) 2, 6-Dichloropyridyl-3-carboxaldehyde 1H-NMR (300 MHz, CDCl3delta TMS): 7.43 (d, J = 8 Hz, 1 H), 8.18 (d, J = 8 Hz, 1 H), 10.35 (s, 1 H).General procedure: Thecorrespondingaldehyde(1.0mmol)wasaddedtoasolutionofN, N'-diphenylethylenediamine (424mg, 2.0mmol)inaqueousethanol(50%, 3mL).Thereactionmixturewasstirredatroomtemperature until the complete consumption of aldehydes, as determined by TLC. The mixture was filtered and the filter cake was washed with a small amount of water and cold ethanol to afford the pure product.General procedure: The corresponding aldehydes (1.0 mmol) were added to a solution of N, N'-dibenzyl ethylenediamine (480 mg, 2.0 mmol) in aqueous ethanol (50%, 3 mL). The reaction mixture was stirred at room temperature until the complete consumption of aldehydes, as determined by thin layer chromatography (TLC). The mixture was ltered and the lter cake was washed with a small amount of water and cold ethanol to aord the pure product.

Molecular Weight:176.00
XLogP3:1.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:174.9591691
Monoisotopic Mass:174.9591691
Topological Polar Surface Area:30
Heavy Atom Count:10
Complexity:131
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes