2-METHOXYPYRIDINE-4-CARBOXALDEHYDE Chemical Properties

Melting point:

33-36 °C

Boiling point:

234.6±20.0 °C(Predicted)

Density 

1.159±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

1.43±0.10(Predicted)

color 

White to off-white

InChI

InChI=1S/C7H7NO2/c1-10-7-4-6(5-9)2-3-8-7/h2-5H,1H3

InChIKey

VOCKNCWQVHJMAE-UHFFFAOYSA-N

SMILES

C1(OC)=NC=CC(C=O)=C1

Safety Information

HS Code 

2933399990

2-METHOXYPYRIDINE-4-CARBOXALDEHYDE Usage And Synthesis

Synthesis

Lithium aluminum hydride (1.9 g, 49 mmol) was added batchwise to a solution of 2-methoxyisonicotinic acid (5.0 g, 33 mmol) in tetrahydrofuran (40 mL) at 0 °C. The reaction mixture was stirred continuously at 0 °C for 1 h, followed by slow dropwise addition of saturated sodium sulfate solution for quenching. The reaction solution was filtered and the filtrate was extracted with ethyl acetate and the organic layer was washed with saturated brine and subsequently concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane (30 mL) and chromium trioxide pyridine complex (10.6 g, 49 mmol) was added. The mixture was stirred at room temperature for 2 h. After completion of the reaction, the mixture was filtered through a short silica gel column and eluted with ethyl acetate. The eluate was concentrated under reduced pressure to remove the solvent. The residue was purified by column chromatography (petroleum ether: ethyl acetate = 10:1) to afford the target product 2-methoxypyridine-4-aldehyde (646 mg, 14% yield). The product was characterized by 1H NMR (CDCl3): δ 10.01 (1H, s), 8.36 (1H, d, J = 5.2 Hz), 7.29 (1H, dd, J = 1.2 Hz, 5.2 Hz), 7.14 (1H, d, J = 1.2 Hz), 3.99 (3H, s).

References

[1] Journal of Organic Chemistry, 1989, vol. 54, # 23, p. 5580 - 5585
[2] Patent: EP2816032, 2014, A1. Location in patent: Paragraph 0458
[3] Patent: EP2862571, 2015, A1. Location in patent: Paragraph 0103; 0104
[4] Patent: US2016/168139, 2016, A1. Location in patent: Paragraph 0942; 0943

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