4-Ethoxy-2-pyridinecarboxylic acid ethyl ester

A solution of 4-chloropicolinic acid (3.0 g, 19.04 mmol) in EtOH (100 mL) was mixed with H^SOA solution of 4-chloropicolinic acid (3.0 g, 19.04 mmol) in EtOH (100 mL) was mixed with HStep-1 : Ethyl 4-ethoxypicolinate: A solution of 4-chloropicolinic acid (1.0 g, 6.35 mmol) and sulphuric acid (0.2 mL, 3.75 mmol) in ethanol (10 mL) was heated to 85°C and maintained for 16 h. Reaction mixture was cooled to RT and the solvent was evaporated under vacuum. The residue was taken into ethyl acetate (20 mL) and basified with aqueous saturated sodium bicarbonate (pH 10, 20 mL). The layers were separated and the organic layer was washed with brine (15 mL), dried (NaA solution of 4-chloropicolinonitrile (5.5 g, 39.7 mmol) in saturated HCI/EtOH solution (80 mL) was stirred at 80 °C for 2 days. The solvent was removed under reduced pressure, saturated aqueous NaHCO.3 (200 mL) was added and the aqueous layer extracted with DCM (3 x 200 mL). The pooled organic extracts were dried (Na2S0To a solution of A solution of 4-chloropicolinonitrile (5.5 g, 39.7 mmol) in saturated HCI/EtOH solution (80 mL) was stirred at 80 C for 2 days. The solvent was removed under reduced pressure, saturated aqueous NaHCO.3 (200 mL) was added and the aqueous layer extracted with DCM (3 x 200 mL). The pooled organic extracts were dried (Na2S04) and concentrated to give the title compound as a white solid (2.6 g, 34%). 1H NMR (400 MHz, CDCb) delta 8.52 (d, J = 5.6 Hz, 1 H), 7.63 (d, J = 2.4 Hz, 1 H), 6.93-6.91 (m, 1 H), 4.80-4.43 (m, 2H), 4.16-4.1 1 (m, 2H), 1.46-1 .41 (m, 6H). LCMS-C: RT 1 .35 min; m/z 196.1 [M+H]+Step-2: 4-Ethoxypicolinohydrazide: To a 0 C cooled solution of To a solution of

Molecular Weight:195.21
XLogP3:1.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:195.08954328
Monoisotopic Mass:195.08954328
Topological Polar Surface Area:48.4
Heavy Atom Count:14
Complexity:184
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes