2,3-DICHLOROPYRIDINE-4-CARBOXYLIC ACID

2, 3-Dichloro-isonicotinic acid[00195] To a solution of diisopropylamine (7.0 niL, 50 mmol) in anhydrous THF (100 rnL) at -25°C was added a 1.6M solution of nBuLi in hexanes (31 rnL, 50 mmol) dropwise under an inert atmosphere. The reaction mixture was then cooled to -78°C and 2, 3- dichloropyridine was added. The reaction mixture was stirred at -78°C for 3 hours, then poured onto solid carbon dioxide and aged for 18 hours at room temperature. The mixture was diluted with water (100 mL) and washed with diethyl ether (3 x 40 mL) then cooled to 0To a solution of diisopropylamine (21. Gg, 213 mmol) and n-butyllithium in hexane (137 ml, 214 mmol) in tetrahydrofuran (600 ml) was added 2, 3-dichloropyridine (30.0 g, 203 mmol) in tetrahydrofuran at -78 2, 3-Dichloro-isonicotinic acid[00195] To a solution of diisopropylamine (7.0 niL, 50 mmol) in anhydrous THF (100 rnL) at -25C was added a 1.6M solution of nBuLi in hexanes (31 rnL, 50 mmol) dropwise under an inert atmosphere. The reaction mixture was then cooled to -78C and 2, 3- dichloropyridine was added. The reaction mixture was stirred at -78C for 3 hours, then poured onto solid carbon dioxide and aged for 18 hours at room temperature. The mixture was diluted with water (100 mL) and washed with diethyl ether (3 x 40 mL) then cooled to 00C, acidified with concentrated HCl (ca. 5 mL) and extracted with diethyl ether (3 x 50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated to give the title compound as a white solid (7.7 g, 80%). 1H NMR (d6-DMSO, 400MHz) 8.49 (d, J = 5.0 Hz, IH), 7.72 (d, J = 5.0 Hz, IH).

Molecular Weight:192.00
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:190.9540837
Monoisotopic Mass:190.9540837
Topological Polar Surface Area:50.2
Heavy Atom Count:11
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes