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| | 3-Amino-2-chloro-4-methylpyridine Basic information |
| | 3-Amino-2-chloro-4-methylpyridine Chemical Properties |
| Melting point | 65-70 °C | | Boiling point | 283.3±35.0 °C(Predicted) | | density | 1.260±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,2-8°C | | solubility | Chloroform, Ethanol | | pka | 3.22±0.10(Predicted) | | form | Crystals | | color | Off White | | InChI | InChI=1S/C6H7ClN2/c1-4-2-3-9-6(7)5(4)8/h2-3H,8H2,1H3 | | InChIKey | UOBCYTOUXLAABU-UHFFFAOYSA-N | | SMILES | C1(Cl)=NC=CC(C)=C1N | | CAS DataBase Reference | 133627-45-9(CAS DataBase Reference) |
| | 3-Amino-2-chloro-4-methylpyridine Usage And Synthesis |
| Chemical Properties | Off White Crystals | | Uses | 3-Amino-2-chloro-4-methylpyridine, also known as CAPIC, is a key intermediate in the production of nevirapine, a non-nucleosidic reverse transcriptase inhibitor that has been established to be clinically useful for the treatment of infection by HIV-1. | | Preparation |
An improved and commercially valuable process is developed by Ge et al. for the scalable synthesis of 2-chloro-3-amino-4-methylpyridine (CAPIC), a key intermediate of Nevirapine. The synthesis was accomplished in four steps, featuring condensation starting from 4,4-dimethoxyl-2-butanone and cyanoacetamide with ammonium acetate and acetic acid as catalysts. Specifically, a stirred solution of NaOH (15.6 g, 0.39 mol) and water (85 g) at 10 ℃ was added, 10% NaClO (96.8 g, 0.13 mol) and ethanol (80 g). 2-Chloro-3-amido-4- methylpyridine 7 (22 g, 0.13 mol) was added to the reaction mixture, stirring for 1 h. The mixture was heated to 60 ℃ and held for 3 h. After ethanol was removed in a vacuum, the mixture was cooled with an ice-water bath for 15–20 min to precipitate solid. Then, the mixture was filtered, washed with water, and dried to give 15.8 g (85.1% yield) of light yellow solid. 14.7 g of the white solid 2 was obtained via recrystallization in toluene.
| | References | [1] Xin Ge. “A concise synthesis of 2-chloro-3-amino-4-methylpyridine.” Research on Chemical Intermediates 37 6 (2011): 599–604. |
| | 3-Amino-2-chloro-4-methylpyridine Preparation Products And Raw materials |
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