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| | 2-Amino-5-chloropyridine-3-carboxylic acid Basic information |
| Product Name: | 2-Amino-5-chloropyridine-3-carboxylic acid | | Synonyms: | 2-Amino-6-chloronicotinic acid 97%;100006;2-Amino-6-chloropyridine-3-carboxylicacid;2-Amino-6-chloronicotinic...;3-Pyridinecarboxylic acid, 2-aMino-6-chloro-;2-Amino-6-chloro-3-pyridinecarboxylic acid;58584-92-2;2-Amino-6-chloropyridin-3-carboxylic acid | | CAS: | 58584-92-2 | | MF: | C6H5ClN2O2 | | MW: | 172.57 | | EINECS: | | | Product Categories: | | | Mol File: | 58584-92-2.mol |  |
| | 2-Amino-5-chloropyridine-3-carboxylic acid Chemical Properties |
| Melting point | 195-197°(dec) | | Boiling point | 383.3±42.0 °C(Predicted) | | density | 1.577±0.06 g/cm3 (20 ºC 760 Torr) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | pka | 3.98±0.10(Predicted) | | form | solid | | Appearance | Off-white to light brown Solid | | InChIKey | INERBKPRIWEQRQ-UHFFFAOYSA-N |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 2936290000 |
| | 2-Amino-5-chloropyridine-3-carboxylic acid Usage And Synthesis |
| Uses | 2-Amino-6-chloronicotinic Acid is a useful synthetic intermediate. It is used in the synthesis of thiamine antagonist transketolase inhibitors. It is also used to prepare 2-aminonicotinic acid 1-oxides as inhibitors of quinolinic acid synthesis in the mammalian brain. | | Synthesis | The general procedure for the synthesis of 2-amino-6-chloronicotinic acid (Inter.2) using 2,6-dichloronicotinic acid (Inter.I) as starting material is as follows:
1. 2,6-dichloronicotinic acid (Inter.I) (1 equiv.) was mixed with liquid ammonia to prepare a 0.6 M ammonia solution.
2. The suspension is transferred to a pressure vessel, sealed and slowly heated to 130°C. At this temperature, the system pressure reaches 18 bar.
3. The temperature and pressure conditions were maintained for 16 hours.
4. upon completion of the reaction, cool the mixture to room temperature.
5. carefully open the pressure vessel and pour the reaction mixture into ice-cold water (in the same volume as the volume of reactants).
6. Acidify the solution to pH 1-2 using concentrated hydrochloric acid, at which point a precipitate is formed.
7. Warm the acidic mixture to room temperature and continue stirring for 30 minutes.
8. Extract the suspension with ether (400 ml each time, 3 times).
9. The organic extracts were combined, filtered and the filtrate was concentrated under vacuum to give a white solid.
10. The resulting solid was dried over P2O5 to afford the target compound 2-amino-6-chloronicotinic acid (Inter.2) in 90% yield and 96% purity. The product can be used directly without further purification. Mass spectral data: m/z (LC-MS ESP): 173 [M + H]+, retention time R/T = 3.63 min. | | References | [1] Patent: WO2016/198400, 2016, A1. Location in patent: Page/Page column 65
[2] Patent: WO2007/60404, 2007, A1. Location in patent: Page/Page column 57-58
[3] Patent: WO2008/23161, 2008, A1. Location in patent: Page/Page column 99
[4] Patent: US2009/99174, 2009, A1
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1212 - 1216 |
| | 2-Amino-5-chloropyridine-3-carboxylic acid Preparation Products And Raw materials |
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