Uses
Ethyl 2,4-Dihydroxy-6-methylnicotinate, is a building block used for various chemical compounds. It is used for the synthesis of analogs of Lucanthone, having antitumor and bactericidal properties.
Synthesis
The general procedure for the synthesis of ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate from ethyl 3-aminocrotonate and diethyl malonate was as follows: ethyl 3-aminocrotonate (100 g, 0.7752 mol) was added to a reactor, followed by the addition of sodium ethoxide (65 g, 0.9559 mol) and anhydrous ethanol (240 g). The reaction system was slowly heated to 80-90 °C, kept at reflux, and the reaction was stirred at the same temperature for 24 hours. After completion of the reaction, the system was cooled to 50-60 °C and concentrated under reduced pressure to remove about 100 g of ethanol. The concentrated solution was slowly poured into 1000 ml of water, 10 g of alkaline activated carbon was added, stirred for 1 hour and filtered. The filtrate was cooled to below 0°C and the pH was adjusted to 2~3 with ammonium chloride, at which time a large amount of solid precipitated, and the solid was collected by filtration. The resulting solid was dried at 50 to 60°C to give white needle-like crystals of ethyl 2,4-dihydroxy-6-methyl-nicotinate in a yield of 125 g (yield = 81.85%, HPLC purity = 99.5%).
References
[1] Patent: CN106279011, 2017, A. Location in patent: Paragraph 0021; 0022
[2] Chemische Berichte, 1898, vol. 31, p. 766,769
[3] Chemische Berichte, 1898, vol. 31, p. 765
