ChemicalBook CAS DataBase List 3-Bromo-4-hydroxypyridine

3-Bromo-4-hydroxypyridine synthesis

6synthesis methods

Product Name:3-Bromo-4-hydroxypyridine
CAS Number:36953-41-0
Molecular formula:C5H4BrNO
Molecular Weight:174

3-Bromo-4-hydroxypyridine is synthesized from 3-bromo-5 hydroxypyridine by reacting it with ammonia or methylamine.

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36953-41-0
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Yield:36953-41-0 66.2%

Reaction Conditions:

with sulfuric acid;sodium nitrite in water at 0 - 95;

Steps:

5.1.2 Preparation of 3-bromo-4-hydroxypyridine (2)
Concentrated sulfuric acid (85.0mL) and the 3-bromo-4-aminopyridine (113.0g, 0.65mol) were added successively to the distilled water (550.0mL) at 0°C, and then NaNO₂ (63.1g, 0.91mol) aqueous solution (130.0mL) was added drop-wise to maintain the temperature between 0 and 5°C. After stirring at r. t. for 1h, the reaction mixture was heated at 95°C for a further 0.5h. Upon cooling to below 0°C, the mixture was alkalized to pH 6 with saturated sodium hydroxide solution, washed with ethyl acetate (200mL×3) and brine (200mL), dried over anhydrous Na₂SO₄, filtered and concentrated to yield the title compound 2 as a yellow solid (75.1g, 66.2%). MS (ESI) m/z: 173.9 [M+H]⁺

References:

Zhao, Sijia;Zhang, Yu;Zhou, Hongyang;Xi, Shuancheng;Zou, Bin;Bao, Guanglong;Wang, Limei;Wang, Jiao;Zeng, Tianfang;Gong, Ping;Zhai, Xin [European Journal of Medicinal Chemistry,2016,vol. 120,p. 37 - 50]

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