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

874-24-8

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

62733-99-7

A suspension of methanol (150 mL, 0.5 M) of 3-hydroxy-2-pyridinecarboxylic acid (10 g, 72 mmol, 1 eq.) was slowly added dropwise to concentrated sulfuric acid (12 mL, 216 mmol, 3 eq.) at 0 °C. The reaction mixture was stirred under reflux conditions for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. Subsequently, the pH was adjusted to 8.5 with saturated aqueous NaHCO3 and solid NaHCO3. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure to afford methyl 3-hydroxy-2-pyridinecarboxylate as a white solid (10.9 g, 99%). Thin layer chromatography (TLC) showed Rf = 0.3 (petroleum ether/EtOAc 1:1, v/v). Melting point was 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. mass spectra (ESI+): m/z (%): 154 (100) [M + H]+.

67-56-1 Synthesis

67-56-1
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874-24-8 Synthesis

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

62733-99-7
177 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.;Bra?ki, 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
313 suppliers
$14.14/1gm:

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

References