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| | 4,6-DICHLORO-2-METHYL-NICOTINIC ACID ETHYL ESTER Basic information |
| Product Name: | 4,6-DICHLORO-2-METHYL-NICOTINIC ACID ETHYL ESTER | | Synonyms: | 4,6-DICHLORO-2-METHYL-NICOTINIC ACID ETHYL ESTER;4,6-Dichloro-2-methylpyridin-3-carboxylic acid ethyl ester;Ethyl 4,6-dichloro-2-methyl-pyridine-3-carboxylate;4,6-dichloro-2-Methyl-3-carbethoxypyridine;3-Pyridinecarboxylic acid, 4,6-dichloro-2-Methyl-, ethyl ester;4,6-Dichloro-2-methyl-3-pyridinecarboxylic acid ethyl ester;Ethyl 4,6-dichloro-2-methylnicotinate 97%;Ethyl 4,6-dichloro-2-methyl-3-pyridinecarboxylate | | CAS: | 686279-09-4 | | MF: | C9H9Cl2NO2 | | MW: | 234.08 | | EINECS: | | | Product Categories: | Piperazines ,Oxazolines/Oxazolidines | | Mol File: | 686279-09-4.mol |  |
| | 4,6-DICHLORO-2-METHYL-NICOTINIC ACID ETHYL ESTER Chemical Properties |
| Boiling point | 283℃ | | density | 1.320 | | Fp | 125℃ | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | -0.22±0.10(Predicted) | | Appearance | Colorless to light yellow Liquid | | InChI | InChI=1S/C9H9Cl2NO2/c1-3-14-9(13)8-5(2)12-7(11)4-6(8)10/h4H,3H2,1-2H3 | | InChIKey | LNIMLSAAPISOEC-UHFFFAOYSA-N | | SMILES | C1(C)=NC(Cl)=CC(Cl)=C1C(OCC)=O |
| | 4,6-DICHLORO-2-METHYL-NICOTINIC ACID ETHYL ESTER Usage And Synthesis |
| Synthesis Reference(s) | [1] Compounds for the prevention and treatment of cardiovascular diseases. Patent no. US20080188467A1. | | Synthesis | A mixture of malonic acid (20 g, 192 mmol), 2,4,6-trichlorophenol (72 g, 365 mmol), and phosphorus oxychloride (38 mL, 403.2 mmol) was stirred at reflux for 12 h. The reaction mixture was cooled to 70° C. and poured into ice water. The solid was collected by filtration, washed with water, and dried to give malonic acid bis-(2,4,6-trichloro-phenyl)ester (85 g, 95%). A solution of malonic acid bis-(2,4,6-trichloro-phenyl)ester (85 g, 184 mmol) and ethyl 3-aminocrotonate (26.08 g, 201.9 mmol) in bromobenzene (100 mL) was stirred at reflux for 50 min. The reaction mixture was cooled to 50° C. and diluted with EtOAc (260 mL). The solid was collected by filtration, washed with water, and dried to give 4,6-dihydroxy-2-methyl nicotinic acid ethyl ester (31 g, 86%). A solution of 4,6-dihydroxy-2-methyl nicotinic acid ethyl ester (31 g, 157 mmol) in phosphorus oxychloride (60 mL, 629 mmol) was stirred at reflux for 1.5 h. The extra phosphorus oxychloride was removed and the reaction mixture was poured into ice water. The solid was removed by filtration. The filtrate was extracted with dichloromethane (3×100 mL) and concentrated. The residue was further purified by column chromatography, to yield 4,6-dichloro-2-methyl nicotinic acid ethyl ester (16.9 g, 46%). | | References | [1] Patent: WO2011/87776, 2011, A1. Location in patent: Page/Page column 64; 66
[2] Patent: WO2007/16525, 2007, A2. Location in patent: Page/Page column 94-96; 101-103
[3] Patent: US2008/188467, 2008, A1. Location in patent: Page/Page column 26-27; 29-30; 40-41
[4] Patent: US2013/281397, 2013, A1. Location in patent: Paragraph 0451; 0465
[5] Patent: CN103319408, 2016, B. Location in patent: Paragraph 0402-0405 |
| | 4,6-DICHLORO-2-METHYL-NICOTINIC ACID ETHYL ESTER Preparation Products And Raw materials |
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