8-Hydroxyquinoline-2-carboxaldehyde

Chemical Properties

yellow crystalline powder

Uses

8-Hydroxy-2-quinolinecarboxaldehyde (8-hydroxyquinoline-2-carbaldehyde) may be used in the preparation of:

• 8-hydroxy-2-quinoline-1-aminopyrene by Schiff-base reaction with 1-aminopyrene
• (E)-2-((2-(pyridin-2-yl)hydrazono)methyl)quinolin-8-ol by coupling with 2-hydrazinopyridine
• 8-hydroxyquinoline-2-carbaldehyde oxime
• 2-[(8-Hydroxyquinoline)-2-methylaminoethyl]-β-D-glucopyranoside

Definition

ChEBI: 8-hydroxyquinoline-2-carbaldehyde is a hydroxyquinoline.

General Description

8-Hydroxy-2-quinolinecarboxaldehyde can be prepared from 2-methylquinolin-8-ol via oxidation using selenium dioxide.

Synthesis

826-81-3

14510-06-6

General procedure for the synthesis of 8-hydroxyquinoline-2-carbaldehyde from 8-hydroxyquinaldine: Preparation of 3,3'-(1E,1'E)-(propane-1,3-diylbis(aza-1-yl-1-ylidene))bis(methyl-1-ylidene-1-ylidene)diquinolin-8-ol (H2PBIQ). A mixture of 8-hydroxy-2-methylquinoline (4 g, 25 mmol), selenium dioxide (3.5 g, 31 mmol), water (3 mL), and 1,4-diethylene glycol (300 mL) was stirred for 24 h at 80 °C under nitrogen protection. After completion of the reaction, the mixture was cooled, filtered and the filtrate evaporated. The resulting solid was purified by silica gel column chromatography (unfolding solvent was petroleum ether: ethyl acetate, 95:5, v/v) to afford pure yellow needle-like crystals of 8-hydroxyquinoline-2-carbaldehyde. The yield was 90%; 1H NMR (400 MHz, CDCl3): δ10.25 (s, 1H), 8.35 (d, J=8.5 Hz, 1H), 8.18 (s, 1H), 8.09 (d, J=8.5 Hz, 1H), 7.66 (t, J=8.0 Hz, 1H), 7.46 (d, J=8.2 Hz, 1H), and 7.31 (d, J=7.7Hz, 1H).

References

[1] RSC Advances, 2015, vol. 5, # 129, p. 107012 - 107019
[2] Inorganic Chemistry Communications, 2014, vol. 47, p. 13 - 16
[3] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 864 - 879
[4] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6346 - 6353
[5] Dalton Transactions, 2014, vol. 43, # 26, p. 10164 - 10174