6-Aminonicotinaldehyde Chemical Properties

Melting point:

161℃

Boiling point:

309.0±27.0 °C(Predicted)

Density 

1.264±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

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

pka

4.78±0.13(Predicted)

Appearance

Light yellow to yellow Solid

Safety Information

HS Code 

2933399990

6-Aminonicotinaldehyde Usage And Synthesis

Uses

6-Aminopyridine-3-carboxaldehyde is a novel ribonucleotide reductase inhibitor that belongs to the class of metal-binding site affecting ribonucleotide inhibitors that are derivatives of alpa-hetero cyclic carboxaldehyde thiosemicarbazone.

Synthesis

General procedure for the synthesis of 2-amino-5-formylpyridine from 2-amino-5-cyanopyridine: To a solution of 2-amino-5-cyanopyridine (10 g, 83.95 mmol, 1 eq.) in tetrahydrofuran (THF, 150 mL) was slowly added lithium aluminum hydride (LAH, 6.37 g, 167.90 mmol, 2 eq.) at 0 °C. The reaction mixture was stirred continuously at 0 °C for 1.5 hours. Upon completion of the reaction, the reaction was quenched by the addition of saturated sodium sulfate solution at 0 °C followed by the addition of water (100 mL). The reaction mixture was extracted with ethyl acetate (100 mL x 3). The organic layers were combined, washed with saturated brine (30 mL × 1), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 2-amino-5-formylpyridine (7.50 g, 61.42 mmol, 73.16% yield) as a yellow oil.LCMS (ESI) analysis: m/z [M + H]+ Theoretical value for C6H6N2O was 123; measured value 123; retention time (RT) = 0.099 min.

References

[1] Patent: WO2018/209132, 2018, A1. Location in patent: Paragraph 0458; 0489
[2] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 292 - 300
[3] Patent: US2009/143420, 2009, A1. Location in patent: Page/Page column 7
[4] Patent: EP1724263, 2006, A1. Location in patent: Page/Page column 55
[5] Patent: EP3305785, 2018, A1. Location in patent: Paragraph 0177; 0178

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