2,3-Dichloro-6-methoxypyridine

3-Amino-2-chloro-6-methoxypyridine (500 mg, 3.17 mmol) dissolved/suspended in cone. hydrochloric acid (10 ml.) was stirred at -5 °C while a solution of sodium nitrite (1.09 g, 15.82 mmol) in water (5 ml.) was added dropwise over 10 min. The mixture was stirred for a further 10 min before copper chloride (3.13 g, 31.65 mmol) was added portionwise over 5 min. The dark effervescing mixture was stirred at -5 °C for 20 min and then the cooling bath was removed and the mixture stirred at ambient temperature for 3 h. The mixture was diluted with water (100 ml_), basified to pH 10-1 1 by addition of 5N sodium hydroxide (aq.) and extracted with diethyl ether (3 x 5OmL). The combined extracts were washed with brine, dried (MgSO3-Amino-2-chloro-6-methoxypyridine (500 mg, 3.17 mmol) dissolved/suspended in conc. hydrochloric acid (10 mL) was stirred at -5 C. while a solution of sodium nitrite (1.09 g, 15.82 mmol) in water (5 mL) was added dropwise over 10 min. The mixture was stirred for a further 10 min before copper chloride (3.13 g, 31.65 mmol) was added portionwise over 5 min. The dark effervescing mixture was stirred at -5 C. for 20 min and then the cooling bath was removed and the mixture stirred at ambient temperature for 3 h. The mixture was diluted with water (100 mL), basified to pH 10-11 by addition of 5N sodium hydroxide (aq.) and extracted with diethyl ether (3 50 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica gel with EtOAc:heptane (1:9, v/v) as eluent to afford the product as a pale yellow oil (229 mg, 41percent).Data for 2, 3-dichloro-6-methoxypyridine: MS (ESI) m/z: 178 ([M+H]+).

Molecular Weight:178.01
XLogP3:2.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:176.9748192
Monoisotopic Mass:176.9748192
Topological Polar Surface Area:22.1
Heavy Atom Count:10
Complexity:112
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes