| Identification | Back Directory | [Name]
6-CHLORO-3-METHYL-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER | [CAS]
878207-92-2 | [Synonyms]
methyl 6-chloro-3-methylpicolinate
methyl 6-chloro-3-methylpyridine-2-carboxylate
6-Chloro-3-methyl-2-pyridinecarboxylic acid methyl ester
6-CHLORO-3-METHYL-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
Methyl 6-chloro-3-methylpicolinate, 6-Chloro-2-(methoxycar
2-Pyridinecarboxylic acid, 6-chloro-3-methyl-, methyl ester
Methyl 6-chloro-3-methylpicolinate, 6-Chloro-2-(methoxycarbonyl)-3-methylpyridine | [Molecular Formula]
C8H8ClNO2 | [MDL Number]
MFCD12756112 | [MOL File]
878207-92-2.mol | [Molecular Weight]
185.61 |
| Chemical Properties | Back Directory | [Boiling point ]
288.7±35.0 °C(Predicted) | [density ]
1.247±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
wooly crystalline powder | [pka]
-0.53±0.10(Predicted) | [color ]
White | [InChI]
InChI=1S/C8H8ClNO2/c1-5-3-4-6(9)10-7(5)8(11)12-2/h3-4H,1-2H3 | [InChIKey]
XWPSWOKQWBNRDW-UHFFFAOYSA-N | [SMILES]
C1(C(OC)=O)=NC(Cl)=CC=C1C |
| Hazard Information | Back Directory | [Synthesis]
2-(Methoxycarbonyl)-3-methylpyridin-1-en-1-ol salt (500 mg, 2.99 mmol, 1.00 eq.) was used as a starting material and dissolved in phosphoryl chloride (2 mL). The reaction mixture was stirred at 110 °C for 4 hours. Upon completion of the reaction, the reaction was quenched with ice water and the pH was adjusted to 7. Subsequently, the aqueous phase was extracted with ethyl acetate (3 × 10 mL). The organic layers were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:5, v/v) as eluent to afford methyl 6-chloro-3-methylpyridine-2-carboxylate (230 mg, 41% yield) as a white solid.LC-MS (ESI, m/z): 186 [M + H]+. | [References]
[1] Patent: US2015/57260, 2015, A1. Location in patent: Paragraph 1234; 1235
[2] Patent: WO2015/25026, 2015, A1. Location in patent: Page/Page column 268
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1736 - 1739
[4] Patent: WO2014/209727, 2014, A1. Location in patent: Page/Page column 69
[5] Patent: WO2014/205593, 2014, A1. Location in patent: Page/Page column 73 |
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