6-Chloro-5-methoxy-nicotinic acid methyl ester Chemical Properties

Melting point:

99-100 °C

Boiling point:

280.9±35.0 °C(Predicted)

Density 

1.288±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-2.89±0.10(Predicted)

form 

powder

color 

Yellow

InChI

InChI=1S/C8H8ClNO3/c1-12-6-3-5(8(11)13-2)4-10-7(6)9/h3-4H,1-2H3

InChIKey

XPHMEWSKODAWPT-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C(OC)C=C1C(OC)=O

Safety Information

HS Code 

2933399990

6-Chloro-5-methoxy-nicotinic acid methyl ester Usage And Synthesis

Synthesis

The reaction was carried out in acetone (190 mL) at reflux for 6 hours with methyl 6-chloro-5-hydroxynicotinate (1.8 g, 9.6 mmol), iodomethane (2M ether solution, 5.8 mL, 11.6 mmol) and potassium carbonate (2.0 g, 14.5 mmol). Upon completion of the reaction, the reaction mixture was concentrated using a rotary evaporator and subsequently diluted by adding water (100 mL). The resulting white precipitate was collected by filtration and washed with additional water to afford the target product methyl 6-chloro-5-methoxynicotinate as a white solid (1.33 g, 68% yield) with a melting point of 83-85 °C. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) δ 8.60 (d, 1H), 7.77 (d, 1H), 3.98 (s, 3H), 3.96 (s, 3H) and GC-MS (calculated value: C8H8ClNO3 [M]+ 201, measured value: 201).

References

[1] Patent: US2009/131468, 2009, A1. Location in patent: Page/Page column 66
[2] Patent: WO2009/64251, 2009, A1. Location in patent: Page/Page column 140
[3] Patent: US2008/108667, 2008, A1. Location in patent: Page/Page column 10
[4] Patent: US2016/376283, 2016, A1. Location in patent: Paragraph 0493; 0495
[5] Patent: WO2011/48525, 2011, A1. Location in patent: Page/Page column 44

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