3-Pyridinecarboxylic acid, 6-chloro-2-methoxy-, methyl ester Chemical Properties

Boiling point:

262.0±35.0 °C(Predicted)

Density 

1.288±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-1.81±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

3-Pyridinecarboxylic acid, 6-chloro-2-methoxy-, methyl ester Usage And Synthesis

Synthesis

Step 2: Synthesis of methyl 6-chloro-2-methoxynicotinate; Sodium methanol (34.25 g, 0.63 mol) was added one time to a solution of methyl 2,6-dichloronicotinate (105 g, 0.5 mol) in dichloromethane (523 mL) at -5 °C. The reaction mixture was slowly warmed to room temperature over 4 hours. Subsequently, additional sodium methanolate (5.48 g, 0.10 mol) was added and the mixture continued to be stirred for 12 hours. Upon completion of the reaction, the mixture was extracted by adding saturated aqueous sodium bicarbonate (300 mL), water (400 mL) and dichloromethane (300 mL) to the mixture. The organic and aqueous layers were separated and the aqueous layer was washed again with dichloromethane (200 mL). All organic layers were combined, washed with water (500 mL), dried with anhydrous magnesium sulfate, and filtered through diatomaceous earth. The filtrate was concentrated to give an oil, which was cooled and solidified to give the target product methyl 6-chloro-2-methoxynicotinate (95 g, 94% yield). The structure of the product was confirmed by 1H NMR (500 MHz, DMSO-d6): δ 3.81 (3H, s, OCH3), 3.93 (3H, s, COOCH3), 7.21 (1H, d, J = 7.8 Hz, Ar-H), 8.18 (1H, d, J = 7.8 Hz, Ar-H).

References

[1] Patent: WO2010/116282, 2010, A1. Location in patent: Page/Page column 53
[2] Tetrahedron Letters, 2011, vol. 52, # 52, p. 7025 - 7029
[3] Patent: WO2006/112828, 2006, A1. Location in patent: Page/Page column 58
[4] Patent: US2005/119251, 2005, A1. Location in patent: Page/Page column 20; 22
[5] Patent: WO2006/14168, 2006, A1. Location in patent: Page/Page column 47

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