3-HYDROXY-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER synthesis
- 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
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62733-99-7
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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]
874-24-8
293 suppliers
$14.14/1gm:
62733-99-7
164 suppliers
$9.00/250mg
36851-80-6
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874-24-8
293 suppliers
$14.14/1gm:
62733-99-7
164 suppliers
$9.00/250mg
67-56-1
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$7.29/5ml-f
943777-92-2
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62733-99-7
164 suppliers
$9.00/250mg