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| | Methyl 2-chloronicotinate Basic information |
| Product Name: | Methyl 2-chloronicotinate | | Synonyms: | 2-CHLORO-3-PYRIDINECARBOXYLIC ACID METHYL ESTER;Methyl 2-chloronicotinate 98%;2-Chloro-3-pyridinecarboxylic acid methyl ester, 2-Chloro-nicotinic acid methyl ester;2-Chloropyridine-3-carboxylic acid methyl ester;METHYL 2-CHLORONICOT;2-Chloronicotinic Acid Methyl Ester
Methyl 2-Chloro-3-pyridinecarboxylate
2-Chloro-3-pyridinecarboxylic Acid Methyl Ester;Methyl 2-chloropyridine-3-carboxylate, 2-Chloro-3-(methoxycarbonyl)pyridine;METHYL 2-CHLORO-3-PYRIDINECARBOXYLATE | | CAS: | 40134-18-7 | | MF: | C7H6ClNO2 | | MW: | 171.58 | | EINECS: | 254-805-9 | | Product Categories: | pyridine series;pharmacetical;blocks;Carboxes;Pyridines;Pyridine | | Mol File: | 40134-18-7.mol |  |
| | Methyl 2-chloronicotinate Chemical Properties |
| Boiling point | 150 °C/1 mmHg | | density | 1.314 g/mL at 25 °C | | refractive index | n 20/D 1.537 | | Fp | 110 °C | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | Liquid | | pka | -1.39±0.10(Predicted) | | color | Colorless | | CAS DataBase Reference | 40134-18-7(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36 | | Safety Statements | 26 | | WGK Germany | 3 | | Hazard Note | Irritant/Keep Cold | | HS Code | 2933399990 |
| | Methyl 2-chloronicotinate Usage And Synthesis |
| Description | Methyl 2-chloronicotinate is used in proteomics studies. | | Uses | Methyl 2-chloronicotinate serves as a precursor for synthesizing the key intermediate of riociguat via cyclization with hydrazine hydrate, and reacts with morpholine to produce 2-morpholinonicotinic acid[6][7]. It acts as a reagent in the palladium-catalyzed N-arylation of amides during the synthesis of CXCR3 antagonists[8]. | | Synthesis | (1) Preparation of methyl 2-chloronicotinate: 15.0 g (95.2 mmol) of 2-chloronicotinate was dissolved in 150 mL of dichloromethane and 8.37 mL (94.5 mmol) of oxalyl chloride was added slowly and dropwise. Subsequently, N,N-dimethylformamide was added dropwise to the mixture and the reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, 40.1 mL (286 mmol) of triethylamine and 37 mL (914 mmol) of methanol were added dropwise to the reaction mixture under ice-bath cooling conditions and stirring was continued for 30 minutes under ice-bath cooling. The reaction mixture was concentrated under reduced pressure and neutralized by adding aqueous sodium bicarbonate to the residue. The aqueous phase was extracted with ether, the organic phases were combined, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (eluent: ethyl acetate/hexane=1:4) to afford 13.9 g of the target product methyl 2-chloronicotinate as a pale yellow liquid in 86% yield.1H-NMR (CDCl3/TMS, δ ppm): 3.97 (3H, s), 7.33 (1H, dd), 8.17 (1H, dd), 8.53 (1H, dd ). | | References |
[1] Patent: CN105061399, 2017, B. Location in patent: Paragraph 0010; 0029; 0030
[2] Patent: US2011/287937, 2011, A1. Location in patent: Page/Page column 72-73
[3] Patent: WO2007/71900, 2007, A1. Location in patent: Page/Page column 94
[4] Yakugaku Zasshi, 1952, vol. 72, p. 1336,1338
[5] Chem.Abstr., 1953, p. 4336
[6] Zhao, B., Lan, Z., Xu, S., & Xiong, Y. (2017). Synthesis of 2-Chloronicotinic Acid Derivatives. Advances in Computer Science Research. https://doi.org/10.2991/emcm-16.2017.119
[7] Bi, S., Diao, W., Zhou, T., Lin, K., & Zhou, W. (2023). Development of a new synthetic route of the key intermediate of riociguat. Synthetic Communications, 53(21), 1844–1853. https://doi.org/10.1080/00397911.2023.2252539
[8] Chan, J., Burke, B., Baucom, K. D., Hansen, K., Bio, M., Divirgilio, E., Faul, M., & Murry, J. (2011). Synthesis of a CXCR3 Antagonist. Synfacts, 2011(06), 0583–0583. https://doi.org/10.1055/s-0030-1259890
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| | Methyl 2-chloronicotinate Preparation Products And Raw materials |
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