ChemicalBook CAS DataBase List 2-Chloro-5-hydroxypyridine

2-Chloro-5-hydroxypyridine synthesis

9synthesis methods

Product Name:2-Chloro-5-hydroxypyridine
CAS Number:41288-96-4
Molecular formula:C5H4ClNO
Molecular Weight:129.54

188057-24-1

41288-96-4

11B. 6-Chloropyridin-3-yl acetate (11.1 g, 64.7 mmol) from step 11a was dissolved in methanol at room temperature, followed by addition of solid potassium carbonate (4.47 g, 32.4 mmol). The reaction mixture was stirred for 2 hours and the volatiles were removed under reduced pressure. The residue was diluted with ether and water, and the aqueous phase was neutralized to pH 7 by addition of aqueous 1 N hydrochloric acid.The organic and aqueous layers were separated and the aqueous phase was extracted twice with ether. The organic extracts were combined, dried over magnesium sulfate and concentrated to give 2-chloro-5-hydroxypyridine as a white solid (8.03 g, 96% yield): melting point 155 °C; 1H NMR (CD3OD, 300 MHz) δ 7.20-7.28 (m, 2H), 7.88 (m, 1H); mass spectrum (CI/NH3) m/z: 130,132 (M+H) +; 147,149 (M+NH4)+.

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Yield:41288-96-4 96%

Reaction Conditions:

with potassium carbonate in methanol at 20; for 2 h;

Steps:

2 Preparation 2
2-Chloro-5-acetoxypyridine (21.66 g, 126 mmol) was dissolved in 300 mL of methanol and K2CO3(8.70 g, 63 mmol) was added. The reaction was stirred at room temperature for approx. 2 h, then concentrated in vacuo. The residue was diluted with diethyl ether and water, and the aqueous layer was adjusted to neutral pH by the addition of 1N aqueous HCl. Following extraction with diethyl ether, the organics were combined, washed with a solution of saturated aqueous NaCl, dried with MgSO4, and concentrated in vacuo. The resulting yellow solid (15.58 g, 96%) was used without further purification.

References:

Eli Lilly and Company US6696439, 2004, B1 Location in patent:Page column 20

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444120-91-6 Synthesis