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ChemicalBook CAS DataBase List 4-Hydroxypyridine
626-64-2

4-Hydroxypyridine synthesis

7synthesis methods
Pyridine-4-boronic acid

1692-15-5

4-Hydroxypyridine

626-64-2

Under standard reaction conditions, 10 equivalents of CuSO4-5H2O (0.049 g, 0.2 mmol) were mixed with 6.7 mol% EA (20 mg) in methanol, followed by the addition of 2 mmol of pyridine-4-boronic acid. The reaction mixture was placed in a preheated oil bath, maintained at 60 °C with continuous stirring and the reaction was carried out at atmospheric pressure. The progress of the reaction was monitored by TLC and after completion of the reaction, the mixture was washed twice with hot ethyl acetate to remove unreacted reactants and by-products. After removal of hot ethyl acetate by evaporation, the crude product was purified by column chromatography on silica gel (260 mesh) with an eluent ratio of petroleum ether:ethyl acetate (25:75). The recovered catalyst could be used directly in the next round of reaction. The structure of the final product 4-hydroxypyridine was confirmed by 1H NMR and 13C NMR spectra.

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Yield:626-64-2 76%

Reaction Conditions:

with copper(ll) sulfate pentahydrate;ellagic acid in methanol at 60; under 760.051 Torr; for 8 h;Green chemistry;

Steps:

In situ synthesis of Cu NPs-EA composite:
General procedure: In a typical reaction, 10 mol% CuSO4·5H2O, (0.049 g, 0.2 mmol)and 6.7 mol% EA (20 mg) were mixed in methanol followed by2 mmol of phenylboronic acid. This reaction mixture was kept ina preheated oil bath by maintaining the temperature at 60 °C andstirred under atmospheric pressure. After completion of the reac-tion, modified by TLC, the mixture was washed twice with hot ethylacetate to remove the reactant and product. The hot ethyl acetatewas removed from the reaction mixture and the resulting crudeproduct was purified by a column chromatography using silicagel 260 mesh (pet ether:ethyl acetate) ratio (25:75). The recov-ered catalyst was reused for the next run. All the products werecharacterized by1H and13C NMR spectra.

References:

Affrose, Abdullah;Azath, Ismail Abulkalam;Dhakshinamoorthy, Amarajothi;Pitchumani, Kasi [Journal of Molecular Catalysis A: Chemical,2014,vol. 395,p. 500 - 505]

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