Identification | More | [Name]
Ethyl 2,4-dihydroxy-6-methyl-3-pyridinecarboxylate | [CAS]
70254-52-3 | [Synonyms]
2,4-DIHYDROXY-6-METHYL-3-PYRIDINECARBOXYLIC ACID ETHYL ESTER 3-PYRIDINECARBOXYLIC ACID, 2,4-DIHYDROXY-6-METHYL-,ETHYL ESTER BUTTPARK 153\57-17 ETHYL 2,4-DIHYDROXY-6-METHYL-3-PYRIDINECARBONATE ETHYL 2,4-DIHYDROXY-6-METHYL-3-PYRIDINECARBOXYLATE ETHYL 2,4-DIHYDROXY-6-METHYLNICOTINATE ETHYL 2,4-DIHYDROXY-6-METHYLPYRIDINE-3-CARBOXYLATE ETHYL ESTER 2,4-DIHYDROXY-6-METHYL-3-PYRIDINE CARBOXYLIC ACID Ethyl 2,4-dihydroxy-6-methylnicotinate 97% 3-Ethoxycarbonyl-4-hydroxy-6-methyl-2(1H)-pyridinone 2,4-dihoxy-6-methyl-3-pyridine nicotinic acid ethyl ester | [EINECS(EC#)]
676-990-9 | [Molecular Formula]
C9H11NO4 | [MDL Number]
MFCD02929397 | [Molecular Weight]
197.19 | [MOL File]
70254-52-3.mol |
Chemical Properties | Back Directory | [Melting point ]
205 °C | [Boiling point ]
446.0±40.0 °C(Predicted) | [density ]
1.312±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
8.08±0.28(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C9H11NO4/c1-3-14-9(13)7-6(11)4-5(2)10-8(7)12/h4H,3H2,1-2H3,(H2,10,11,12) | [InChIKey]
CMCZAWPDHHYFPU-UHFFFAOYSA-N | [SMILES]
C1(O)=NC(C)=CC(O)=C1C(OCC)=O | [CAS DataBase Reference]
70254-52-3(CAS DataBase Reference) |
Hazard Information | Back Directory | [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 this temperature for 24 hours. Upon 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 basic 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 to 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 |
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