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| | 2-Oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester Basic information |
| Product Name: | 2-Oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester | | Synonyms: | Ethyl 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate;1,2-Dihydro-3-(ethoxycarbonyl)-2-oxo-1,8-naphthyridine;Ethyl 1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylate 95+%;3-ethoxycarbonyl-1,8-naphthyridin-2-olate;1,8-Naphthyridine-3-carboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester;Ethyl 1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylate;2-Oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester | | CAS: | 5174-90-3 | | MF: | C11H10N2O3 | | MW: | 218.21 | | EINECS: | | | Product Categories: | DSS | | Mol File: | 5174-90-3.mol | ![2-Oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester Structure](CAS/GIF/5174-90-3.gif) |
| | 2-Oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester Chemical Properties |
| Melting point | 214.8-215.0°C | | storage temp. | Sealed in dry,Room Temperature | | form | solid | | InChI | 1S/C11H10N2O3/c1-2-16-11(15)8-6-7-4-3-5-12-9(7)13-10(8)14/h3-6H,2H2,1H3,(H,12,13,14) | | InChIKey | PIHWQJBFCRABCQ-UHFFFAOYSA-N | | SMILES | CCOC(=O)C1=Cc2cccnc2NC1=O |
| Hazard Codes | Xi | | HazardClass | IRRITANT | | HS Code | 2932209090 | | Storage Class | 11 - Combustible Solids |
| | 2-Oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester Usage And Synthesis |
| Synthesis | General procedure for the synthesis of ethyl 2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylate from 2-amino-3-pyridinecarboxaldehyde and diethyl malonate: 2-amino-3-pyridinecarboxaldehyde (1.0 g, 8.19 mmol) was suspended in a screw-capped pressure tube containing diethyl malonate (6.2 mL, 41.0 mmol). The reaction tube was sealed by the addition of piperidine (1.6 mL, 16.4 mmol). The reaction mixture was heated to 120°C and the reaction was kept at a constant temperature for 3.0 hours. Upon completion of the reaction, the mixture was allowed to cool to room temperature. The precipitate formed was collected by filtration and washed with ether (Et2O) to afford ethyl 2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylate 1.62 g in 91% yield. The structure of the product was confirmed by 1H NMR (CD3OD): δ 8.64 (m, 1H), 8.62 (s, 1H), 8.22 (m, 1H), 7.32 (m, 1H), 4.38 (m, 2H), 1.40 (t, 3H). | | References | [1] Patent: WO2010/97410, 2010, A1. Location in patent: Page/Page column 121
[2] Patent: US2012/40942, 2012, A1. Location in patent: Page/Page column 56
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 12, p. 3644 - 3651
[4] Archiv der Pharmazie, 2015, vol. 348, # 1, p. 34 - 45
[5] Chemical Biology and Drug Design, 2014, vol. 84, # 6, p. 721 - 731 |
| | 2-Oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester Preparation Products And Raw materials |
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