2,6-Pyridinedicarboxaldehyde

Chemical Properties

White to gray solid

Uses

2,6-Pyridinedicarboxaldehyde has been used in preparation of:

• functionalized resin Amberlite XAD-4
• boron-dipyrromethene (BODIPY)-based fluorescence probe with a N,N′-(pyridine-2, 6-diylbis(methylene))-dianiline substituent
• novel N-heterocyclic chitosan aerogel derivatives

Uses

2,6-Pyridinedicarboxaldehyde is an intermediate used to prepare functionalized resin Amberlite XAD-4,boron-dipyrromethene (BODIPY)-based fluorescence probe with a N,N′-(pyridine-2, 6-diylbis(methylene))-dianiline substituent and novel N-heterocyclic chitosan aerogel derivatives.

Synthesis

69839-04-9

5431-44-7

General procedure for the synthesis of 2,6-pyridinedicarboxaldehyde from the compound (CAS: 69839-04-9): to a stirring LiAlH4 solution (0.31 g, 8.24 mmol; dissolved in 3 mL of anhydrous THF) at 0 °C, slowly add dropwise 2,6-bis(1-pyrrolidinocarbonyl)pyridine (3.0 g, 11 mmol) to anhydrous THF ( 20 mL) solution. The reaction mixture was stirred in 30 mL of anhydrous THF for 16 h. After 40 min, the reaction mixture was carefully hydrolyzed with 2 M aqueous hydrochloric acid. The organic phase was separated and the aqueous phase was extracted with CH2Cl2 (5 x 10 mL). The organic phase was combined and dried with Na2SO4. The solvent was removed in vacuum and the product was recrystallized by ether to give an almost colorless powdered 2,6-pyridinedicarboxaldehyde. The yield was 1.30 g (76% yield).

References

[1] Tetrahedron Letters, 2013, vol. 54, # 3, p. 217 - 219