ChemicalBook CAS DataBase List 3-HYDROXY-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER

3-HYDROXY-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER synthesis

4synthesis methods

Product Name:3-HYDROXY-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
CAS Number:62733-99-7
Molecular formula:C7H7NO3
Molecular Weight:153.14

67-56-1 Synthesis

67-56-1
728 suppliers
$7.29/5ml-f

874-24-8 Synthesis

874-24-8
285 suppliers
$14.14/1gm:

3-HYDROXY-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER

62733-99-7
153 suppliers
$9.00/250mg

Yield:62733-99-7 99%

Reaction Conditions:

with sulfuric acid at 0; for 6 h;Reflux;

Steps:

2.2.1. Synthesis of methyl 3-hydroxypicolinate (Compound 2)
To a suspension of 3-hydroxypicolinic acid 1 (10 g, 72 mmol, 1equiv) in methanol (150 mL, 0.5 M) was added dropwise at 0 °C aconcentrated sulfuric acid (12 mL, 216 mmol, 3 equiv.). The obtainedsolution was stirred at reflux 6 h. The cooled reaction mixture wasconcentrated under reduced pressure. The pH was adjusted at 8.5 withan aqueous solution of saturated NaHCO₃ and solid NaHCO₃. Theaqueous layer was extracted with EtOAc and the combined organiclayer was washed with brine, dried over MgSO₄ and concentrated underreduced pressure to give 2 as a white solid (10.9 g, 99%). Rf=0.3(Petroleum ether/EtOAc 1/1, v/v). m.p. = 74 °C. ¹H NMR (300 MHz,CDCl3): δ (ppm)=4.06 (s, 3H), 7.34 (dd, J=3.9, 8.4 Hz, 1H), 7.38(dd, J=1.5, 8.4 Hz, 1H), 8.38 (dd, J=1.5, 3.9 Hz, 1H), 10.64 (s, 1H).13C NMR (75 MHz, CDCl₃): δ=53.2, 126.3, 129.8, 130.2, 141.6, 158.9,169.9. MS (ESI+): m/z (%): 154 (100) [M+H]+.

References:

Pashirova, Tatiana N.;Braïki, Anissa;Zueva, Irina V.;Petrov, Konstantin A.;Babaev, Vasily M.;Burilova, Evgenia A.;Samarkina, Darya A.;Rizvanov, Ildar Kh.;Souto, Eliana B.;Jean, Ludovic;Renard, Pierre-Yves;Masson, Patrick;Zakharova, Lucia Ya.;Sinyashin, Oleg G. [Journal of Controlled Release,2018,vol. 290,p. 102 - 111]

FullText

874-24-8 Synthesis

874-24-8
285 suppliers
$14.14/1gm:

62733-99-7
153 suppliers
$9.00/250mg

References