2-CHLORO-4-ETHOXYPYRIDINE

A mixture of 2-chloro-4-nitropyridine (170 g 1070 mmol) in THF (2 L) was added NaOEt (109.45 g 1610 mmol) slowly at 0 . The mixture was stirred at 25 for 12 h. LCMS and TLC (PE/EA 51 RTo a mixture of 2-chloro-4-nitropyridine (170 g, 1070 mmol) in THF (2 L) was added sodium ethanolate (109.45 g, 1610 mmol) slowly at 0 °C. The mixture was stirred at 25 °C for 12 h. LCMS and TLC analysis (PE/EA = 5:1, Rf= 0.6) showed the reaction wasfinished. The mixture was filtered, and most of the filtrate solvent was removed by reduced pressure. The mixture was quenched with water and extracted with EA, the organic layer was washed with brine, and then concentrated. Another six batches were34prepared following the same procedure to give 2-chloro-4-ethoxypyridine (1100 g, 7.01 mol, 92.4percent): ‘H NMR (400 MHz, CD3OD) 8.15 (d, J 6.0 Hz, 1H), 6.99 (d, J 2.0 Hz, 1H), 6.91-6.89 (m, 1H), 4.16-4.14 (m, 2H), 1.41-1.38 (m, 3H); ES-LCMS m/z: 158.1 (M+H).Step 1 : 2-Chloro-4-ethoxypyridine To a mixture of 2-chloro-4-nitropyridine (170 g, 1070 mmol) in THF (2 L) was added sodium ethanolate (109.45 g, 1610 mmol) slowly at 0 °C. The mixture was stirred at 25 °C for 12 h. LCMS and TLC analysis (PE/EA = 5: 1, RTo a mixture of 2-chloro-4-nitropyridine (20 g, 126 mmol) in THF (200 mL) was added sodium ethoxide (25.8 g, 378 mmol) in portions. The mixture was stirred at 25 °C for 10 h. The mixture was filtered and the filtrate was concentrated. The crude material was purified by silica column chromatography (PE/EA = 5: 1). All fractions found to contain product by TLC (PE/EA = 5: 1, R6.01.22.01 2-chloro-4-ethoxy-pyridine 33 ml sodium ethoxide was added to 19.2 g 2-chloro-4-iodopyridine in 150 mL ethanol. The reaction was refluxed overnight. Then water was added and extracted with tert-butyl- methylether. The organic layer was evaporated and the residue cleanded by chromatography on silica gel (petrolether/EtOAC:9/l) to yield 5 g of the desired compound. R6.01.22.01

Molecular Weight:157.60
XLogP3:2.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:157.0294416
Monoisotopic Mass:157.0294416
Topological Polar Surface Area:22.1
Heavy Atom Count:10
Complexity:99.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes