| Identification | Back Directory | [Name]
4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER | [CAS]
6975-44-6 | [Synonyms]
NSC 22486
BUTTPARK 153\57-32
SPECS AC-907/34126052
2,4-Dihydroxy-5-(ethoxycar
Ethyl 4,6-dihydroxynicotinate
4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER
2,4-Dihydroxy-5-(ethoxycarbonyl)pyridine
ethyl 2,4-dihydroxypyridine-5-carboxylate
Ethyl 4,6-Dihydroxypyridine-3-carboxylate
4,6-Dihydroxynicotinic acid ethyl ester ,97%
ethyl 6-hydroxy-4-oxo-1H-pyridine-3-carboxylate
Nicotinicacid, 4,6-dihydroxy-, ethyl ester (7CI)
4,6-DIHYDROXYPYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
6-hydroxy-4-oxo-1H-pyridine-3-carboxylic acid ethyl ester
6-hydroxy-4-keto-1H-pyridine-3-carboxylic acid ethyl ester
4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER ISO 9001：2015 REACH
3-Pyridinecarboxylic acid, 1,6-dihydro-4-hydroxy-6-oxo-, ethyl ester
Ethyl 4,6-dihydroxypyridine-3-carboxylate, 4,6-Dihydroxynicotinic acid ethyl ester
Ethyl 4,6-dihydroxypyridine-3-carboxylate, 2,4-Dihydroxy-5-(ethoxycarbonyl)pyridine | [Molecular Formula]
C8H9NO4 | [MDL Number]
MFCD00834976 | [MOL File]
6975-44-6.mol | [Molecular Weight]
183.16 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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