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| | 4, 6-Dihydroxynicotinic acid ethyl ester Basic information |
| Product Name: | 4, 6-Dihydroxynicotinic acid ethyl ester | | Synonyms: | 2,4-Dihydroxy-5-(ethoxycar;4,6-DIHYDROXYPYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER;BUTTPARK 153\57-32;SPECS AC-907/34126052;Ethyl 4,6-dihydroxynicotinate;ethyl 6-hydroxy-4-oxo-1H-pyridine-3-carboxylate;6-hydroxy-4-keto-1H-pyridine-3-carboxylic acid ethyl ester;6-hydroxy-4-oxo-1H-pyridine-3-carboxylic acid ethyl ester | | CAS: | 6975-44-6 | | MF: | C8H9NO4 | | MW: | 183.16 | | EINECS: | | | Product Categories: | Pyridine | | Mol File: | 6975-44-6.mol |  |
| | 4, 6-Dihydroxynicotinic acid ethyl ester Chemical Properties |
| Melting point | 214-217° | | Boiling point | 339.4±42.0 °C(Predicted) | | density | 1.380 | | storage temp. | Inert atmosphere,Room Temperature | | form | powder to crystal | | pka | 4.50±1.00(Predicted) | | color | White to Orange to Green | | InChI | InChI=1S/C8H9NO4/c1-2-13-8(12)5-4-9-7(11)3-6(5)10/h3-4H,2H2,1H3,(H2,9,10,11) | | InChIKey | QDHHLXABEXNRJX-UHFFFAOYSA-N | | SMILES | C1NC(=O)C=C(O)C=1C(OCC)=O | | CAS DataBase Reference | 6975-44-6 |
| | 4, 6-Dihydroxynicotinic acid ethyl ester Usage And Synthesis |
| Chemical Properties | White solid | | Uses | Ethyl 4,6-dihydroxynicotinate has been used as a reactant is the synthesis of pyridazinopyrimidinone and pyridopyrimidinone derivatives as PDE5 inhibitors and for the synthesis of pyridone diaryl ether non-nucleoside inhibitors of HIV-1 reverse transcriptase. | | Synthesis | The general procedure for the synthesis of ethyl 4,6-dihydroxynicotinate from ethanoic anhydride and diethyl 1,3-acetone dicarboxylate was as follows: diethyl 3-oxoglutarate (101 g, 0.5 mol), triethyl orthoformate (81.4 g, 0.55 mol), and acetic anhydride (102 g, 1 mol) were mixed and the reaction was maintained at a temperature of 120 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and dissolved in dichloromethane (1 L). Subsequently, the solution was cooled to 0 °C, 30% ammonia (80 mL) was slowly added, and then the reaction mixture was gradually warmed to room temperature and left overnight. The reaction mixture was extracted twice with water and the aqueous phase was adjusted to pH 5 with concentrated hydrochloric acid. after acidification, the precipitate was collected by filtration to afford ethyl 4,6-dihydroxynicotinate (60.0 g, 60% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.99 (s, 1H), 5.58 (s, 1H), 4.23 (q, J = 6.8, 14.0 Hz, 2H), 1.25 (t, J = 7.2 Hz, 3H); MS (ESI) m/z: 184.1 [M + H]+. | | References | [1] Patent: US8461179, 2013, B1. Location in patent: Page/Page column 66 |
| | 4, 6-Dihydroxynicotinic acid ethyl ester Preparation Products And Raw materials |
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