ChemicalBook CAS DataBase List 2-Chloro-4-hydroxypyridine

2-Chloro-4-hydroxypyridine synthesis

7synthesis methods

Product Name:2-Chloro-4-hydroxypyridine
CAS Number:17368-12-6
Molecular formula:C5H4ClNO
Molecular Weight:129.54

14432-12-3 Synthesis

14432-12-3
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17368-12-6
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Yield:17368-12-6 92%

Reaction Conditions:

Stage #1:4-Amino-2-chloropyridine with sulfuric acid;sodium nitrite in water at 0 - 20; for 24 h;
Stage #2: with sodium hydroxide in water

Steps:

1
In a recovery flask, 4-amino-2-chloropyridine (3.0 g, 23.3 mmol) was dissolved in 40% sulfuric acid (50 g) . While the solution was stirred at 0⁰C, sodium nitrite (1.93 g, 28.0 mmol) was added. The mixture was stirred at room temperature for 24 hours. After the reaction completed, the reaction liquid was neutralized by adding an aqueous sodium hydroxide solution and an aqueous sodium hydrogencarbonate solution. The organic phase was extracted with ethyl acetate. The organic phase was then dried over magnesium sulfate, filtered, distilled to remove the solvent, and dried under reduced pressure to give 2-chloro-4-hydroxypyridine (light brown solid). The solid weighed 2.78 g, and the yield was 92%. [0088]¹H-NMR (270 MHz, DMSO-d6) ppm: 11.20 (s, IH, -OH), 8.09 (d, IH, J = 5.4 Hz, ArH), 6.81 (s, IH, ArH), 6.77 (d, IH, J = 2.2 Hz, ArH)

References:

SHOWA DENKO K.K. WO2009/11447, 2009, A2 Location in patent:Page/Page column 37-38

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