6-Chloro-4-methoxypyridine-3-carbaldehyde Chemical Properties

Boiling point:

301.9±37.0 °C(Predicted)

Density 

1.317±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.26±0.10(Predicted)

form 

powder

color 

White

InChI

InChI=1S/C7H6ClNO2/c1-11-6-2-7(8)9-3-5(6)4-10/h2-4H,1H3

InChIKey

MJKBQIXGOHBBFO-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

6-Chloro-4-methoxypyridine-3-carbaldehyde Usage And Synthesis

Synthesis

Sodium methanolate (0.068 g, 1.25 mmol) was added batchwise to a stirred solution of 4,6-dichloropyridine-3-carbaldehyde (0.2 g, 1.14 mmol) in methanol (10 mL) at 0 °C. The reaction mixture was slowly warmed to room temperature (about 5 hours) and stirring was continued at room temperature for 16 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was dissolved in dichloromethane. Insoluble solids were removed by filtration and the filtrate was purified by fast silica gel column chromatography with an elution gradient of 0 to 50% ethyl acetate in heptane solution. The purified grades were collected and concentrated under reduced pressure to give 6-chloro-4-methoxynicotinaldehyde (0.111 g, 57% yield) as a white solid.1H NMR (500 MHz, CDCl3, 22 °C) δ 4.02 (3H, s), 6.97 (1H, s), 8.69 (1H, s), 10.37 (1H, d). Mass spectrum (ESI+): m/z 172 [M+H]+.

References

[1] Patent: WO2018/19793, 2018, A1. Location in patent: Page/Page column 126; 127

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