4-Chloropyridine-2-carboxylic acid ethyl ester

Step-1 : Ethyl-4-chloroypicolinate: A mixture of 4-chloropicolinic acid (20 g, 127 mmol) and thionyl chloride (200 mL) was heated to 100 °C and maintained for 6 h. The reaction was cooled to RT, and the excess of thionyl chloride was removed under vacuum. To the above obtained residue was then added ethanol (200 mL) at 0 °C drop-wise and the resulting mixture was stirred at RT for 20 h.The solvent was evaporated under vacuum and the residue was taken in ethyl acetate (1000 mL), washed with water (2x500 mL), saturated sodium bicarbonate solution (2x500 mL), brine (500 mL), dried (Na(Reference Example A-1) Ethyl 4-chloropyridine-2-carboxylate (Production Example 15) Ethyl 4-chloropyridine-2-carboxylate Step-1 : Ethyl-4-chloroypicolinate: A mixture of 4-chloropicolinic acid (20 g, 127 mmol) and thionyl chloride (200 mL) was heated to 100 °C and maintained for 6 h. The reaction was cooled to RT, and the excess of thionyl chloride was removed under vacuum. To the above obtained residue was then added ethanol (200 mL) at 0 °C drop-wise and the resulting mixture was stirred at RT for 20 h.The solvent was evaporated under vacuum and the residue was taken in ethyl acetate (1000 mL), washed with water (2x500 mL), saturated sodium bicarbonate solution (2x500 mL), brine (500 mL), dried (NaStep 1: (Reference Example A-1) Ethyl 4-chloropyridine-2-carboxylate To a stirred solution of 4-chloropicolinic acid (15.0 g, 95.20 mmol, 1.0 equiv) in ethanol (225.0 mL, 15.0 vol. equiv) was added sulfuric acid (34.4 mL, 619 mmol, 6.5 equiv). (0376) The resulting mixture was stirred for 2 h at reflux. The completion of reaction was monitored by TLC. The solvent was removed under reduced pressure. The residue was treated with DM water (0377) (500.0 mL) and extracted with EtOAc (2 x 500 mL). The combined organic extract was washed with brine (200.0 mL), saturated solution of sodium bicarbonate (500.0 mL), dried over Na(Production Example 15) Ethyl 4-chloropyridine-2-carboxylate

Molecular Weight:185.61
XLogP3:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:185.0243562
Monoisotopic Mass:185.0243562
Topological Polar Surface Area:39.2
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes