2-Chloro-4-quinolinecarboxylic acid

2-Hydroxyquinoline-4- carboxylic acid (34, 2.57 g, 13.6 MMOL) and POCI3 (25 mL) were refluxed for 24 h. The reaction mixture was poured onto crushed-ice (300 g). The solid that separated was filtered, washed with water, and dried well under high vacuum afforded 2.47 g (87percent) white flasks of desired PRODUCT. 1H NMR (CDCI3, 300 MHz): 8 8.67 (d, 1H, J = 8.4 Hz), 7.91 (d, 1H, J = 8.1 Hz), 7.83 (s, 1H), 7.67 (t, 1H, J = 7.2 Hz), 7.54 (t, 1H, J = 7.2 Hz); LCMS (m/z): 208 (MH+).Reference Example 24: Synthesis of a) 2-Chloroquinoline-4-carbonyl chloride; General procedure: To cinconinic acid (1.7 g, 9.0 mmol) was added POCl3 (10 mL) under cooling and then heated to reflux for 3 h under nitrogen. The mixture was cooled to room temp, poured into ice-water and extracted with CHCl3. The combined extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. To the residue was added thionyl chloride (10 mL), and the resulting mixture was heated to reflux under nitrogen for 2 h. The excess of thionyl chloride was then removed under reduced pressure, and ethanol (20 mL) / methanol, triethylamine (6 mL) were added at 0C. The resulting reaction mixture was heated to reflux for 30 min. The excess of alcohol was distilled off completely, and the mixture was extracted with CHCl3. The organic layer was collected, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the desired product (1.4 g, 70% yield).c)

Molecular Weight:207.61
XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:207.0087061
Monoisotopic Mass:207.0087061
Topological Polar Surface Area:50.2
Heavy Atom Count:14
Complexity:234
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes