3-CHLORO-4-HYDROXYPYRIDINE

In a 500 ml four-necked flask equipped with a stirring, thermometer, and reflux condenser, 130 grams of methanol, 12.0 g (0.05 mol) of 3, 3, 5-trichloropiperidin-4-one obtained in Example 3, 4.1 grams of sodium hydroxide, Stir the reaction at 40-45 C for 2 hours.Cool to 20-25 , Filtered, the filter cake was washed with 20 g of solvent, the filtrates were combined, and the solvent was recovered by distillation, 5.74 g of 3-chloro-4-hydroxypyridine were obtained as a white solid, The yield is 88.6% (the yield is based on piperidin-4-one hydrochloride), The liquid purity was 99.3%.Step A. 3-Chloro-4-methoxypyridine A solution of 2.0 M trimethylsilyldiazomethane in hexane (21.9 mL, 43.8 mmol) was added slowly to a suspension of 3-chloropyridin-4-ol (4.00 g, 30.9 mmol) in toluene (213.9 mL) and MeOH (32.1 mL) at 0 C. After 30 min. at 0 C., the reaction mixture was warmed to room temperature and stirred for 64 h. Aqueous AcOH was added and then enough saturated aq. Na2CO3 was added to bring the pH to 7.5. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting brown oil was purified on 40 g silica gel (2:1 DCM/EtOAc) to afford 2.5 g (56% yield) of the sub-title compound. LCMS calc. for C6H7ClNO (M+H)+: m/z=144.0. found: 144.1.

Molecular Weight:129.54
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:128.9981414
Monoisotopic Mass:128.9981414
Topological Polar Surface Area:29.1
Heavy Atom Count:8
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes