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Ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

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Ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate Basic information
Product Name:Ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate
Synonyms:ETHYL 4-HYDROXY-6-METHYL-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBOXYLATE;ETHYL-4-HYDROXY-6-METHYL-2-PYRIDONE-3-CARBOXYLATE;AURORA KA-3793;1,2-Dihydro-4-hydroxy-6-methyl-2-(oxo)nicotinic acid ethyl ester;1,2-Dihydro-4-hydroxy-6-methyl-2-oxo-3-pyridinecarboxylic acid ethyl ester;4-Hydroxy-6-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid ethyl ester;3-Pyridinecarboxylic acid, 1,2-dihydro-4-hydroxy-6-methyl-2-oxo-, ethyl ester;3-Pyridinecarboxylic acid, 1,2-dihydro-4-hydroxy-6-methyl-2-oxo-, ethyl ester (9CI, ACI)
CAS:10350-10-4
MF:C9H11NO4
MW:197.19
EINECS:
Product Categories:New Products for Chemical Synthesis;Pyridines;Building Blocks;C9;Chemical Synthesis;Heterocyclic Building Blocks
Mol File:10350-10-4.mol
Ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate Structure
Ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate Chemical Properties
Melting point 216-222°C
Boiling point 362.9±42.0 °C(Predicted)
density 1.308±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka4.50±1.00(Predicted)
AppearanceWhite to light yellow Solid
Safety Information
Hazard Codes Xn
Risk Statements 22-36/37/38
Safety Statements 22-26-36/37/39
MSDS Information
Ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate Usage And Synthesis
UsesEthyl 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
ETHYL 3-AMINOCROTONATE

626-34-6

Diethyl malonate

105-53-3

ETHYL 4-HYDROXY-6-METHYL-2-OXO-1,2-DIHYDROPYRIDINE-3-CARBOXYLATE

10350-10-4

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
Ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate Preparation Products And Raw materials
Raw materialsEthyl 3-aminocrotonate-->Diethyl malonate-->Ethanol-->Sodium ethoxide
Tag:Ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate(10350-10-4) Related Product Information
Nicotinic acid ETHYL STEARATE Ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate Methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate AURORA KA-5524 AURORA KA-5497 3-Pyridinecarboxylic acid,1,2-dihydro-4-hydroxy-5,6-dimethyl-2-oxo-,ethyl ester AURORA KA-5270