|
|
| | 2-Chloro-6-pyrazinecarboxylic acid methyl ester Basic information |
| Product Name: | 2-Chloro-6-pyrazinecarboxylic acid methyl ester | | Synonyms: | 2-Chloro-6-pyrazinecarboxylic acid methyl ester;6-Chloropyrazine-2-carboxylic acid methyl ester;Methyl 6-chloropyrazine-2-carboxylate;METHYL 6-CHLORO-2-PYRAZINECARBOXYLATE;m90108;6-Chloro-pyrazine-2-carbo...;6-Chloro-pyrazine -2-carboxylate;methyl 6-chloro-2-pyrazinecarboxylate(SALTDATA: FREE) | | CAS: | 23611-75-8 | | MF: | C6H5ClN2O2 | | MW: | 172.57 | | EINECS: | | | Product Categories: | | | Mol File: | 23611-75-8.mol |  |
| | 2-Chloro-6-pyrazinecarboxylic acid methyl ester Chemical Properties |
| Melting point | 40-41 °C | | Boiling point | 60-70 °C(Press: 30 Torr) | | density | 1.372±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | -2.28±0.10(Predicted) | | form | Solid | | Appearance | Light yellow to brown Solid | | InChI | InChI=1S/C6H5ClN2O2/c1-11-6(10)4-2-8-3-5(7)9-4/h2-3H,1H3 | | InChIKey | MVVYUJFEXRODQA-UHFFFAOYSA-N | | SMILES | C1(C(OC)=O)=NC(Cl)=CN=C1 |
| | 2-Chloro-6-pyrazinecarboxylic acid methyl ester Usage And Synthesis |
| Synthesis | The product of Example 1D (7.18 g, 45.9 mmol) was taken as raw material and dissolved in dichlorosulfoxide (SOCl2, 50 mL, 687 mmol). The reaction mixture was heated to reflux and kept for 8 hours and then cooled to room temperature. Excess SOCl2 was evaporated under reduced pressure followed by slow addition of water (50 mL) at 0 °C to quench the reaction. The reaction mixture was neutralized with 1 M aqueous potassium carbonate (K2CO3, aq), followed by multiple extractions with dichloromethane (CH2Cl2, 5 × 100 mL). All organic phase extracts were combined, washed with saturated saline (100 mL), dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: 5% ethyl acetate in dichloromethane solution, Rf=0.35) to afford methyl 6-chloropyrazine-2-carboxylate as a thick oil, which gradually solidified after standing (7.16 g, 67% yield). The product was characterized by 1H NMR (DMSO-d6, 300 MHz): δ 3.94 (s, 3H), 9.07 (s, 1H), 9.19 (s, 1H). Mass spectrum (DCI/NH3) showed m/z 190 (M+NH4)+. | | References | [1] Patent: US2009/281118, 2009, A1. Location in patent: Page/Page column 10-11
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 22, p. 7816 - 7825
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7678 - 7692 |
| | 2-Chloro-6-pyrazinecarboxylic acid methyl ester Preparation Products And Raw materials |
|