Methyl 3-chloroisonicotinate Chemical Properties

Boiling point:

70-75℃ (0.1 Torr)

Density 

1.294±0.06 g/cm3(Predicted)

refractive index 

1.53425 (589.3 nm 20℃)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

0.83±0.18(Predicted)

Appearance

Colorless to light yellow Liquid

Safety Information

HS Code 

2933399990

Methyl 3-chloroisonicotinate Usage And Synthesis

Synthesis

The general procedure for the synthesis of methyl 3-chloroisonicotinate from 3-chloropyridine-4-carboxylic acid and iodomethane was as follows: potassium carbonate (36.3 g, 263 mmol) was added to 3-chloropyridine-4-carboxylic acid (10.35 g, 65.7 mmol) dissolved in DMSO (50 mL). After 30 min of reaction, iodomethane (8.22 mL, 131 mmol) was slowly added. The reaction mixture was stirred continuously at room temperature for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride solution (300 mL) and deionized water (200 mL), followed by extraction with ethyl acetate (3 x 200 mL). The organic phases were combined, washed with brine (2 × 50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent. Purification by silica gel column chromatography with the eluent being a hexane solution of 10-30% ethyl acetate resulted in methyl 3-chloroisonicotinate as a colorless liquid (6.275 g, 56% yield). MS (electrospray positive ion mode) m/z: 172 ([M+H]+); LC retention time: 2.45 min (analytical conditions).

References

[1] Patent: WO2009/100171, 2009, A1. Location in patent: Page/Page column 70
[2] Synthetic Communications, 1997, vol. 27, # 6, p. 1075 - 1086

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