4-Quinolinecarboxaldehyde, 8-hydroxy- synthesis
- Product Name:4-Quinolinecarboxaldehyde, 8-hydroxy-
- CAS Number:14510-07-7
- Molecular formula:C10H7NO2
- Molecular Weight:173.17
111115-16-3
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Yield:14510-07-7 83.3%
Reaction Conditions:
with hydrogenchloride;water in dichloromethane at 20; for 48 h;
Steps:
Synthesis of 4-carbaldehyde-8-hydroxyquinoline (4)
A solution of 4-carbaldehyde-8- benzyloxyquinoline (1.3 g, 4.94 mmol) in CH2Cl2 (14 ml) was added with hydrochloric acid (37%, 7 ml). The mixture was stirred for 48 h at room temperature and then neutralized with aqueous sodium hydroxide solution. It was extracted with ethyl acetate, dried with anhydrous MgSO4 and then the solvent was removed on a rotary evaporator. The crude product was purified by a column chromatography (silica gel) with the mixture of CH2Cl2 and methanol (99:1, v/v) as the eluent, giving a yellow solid (0.71 g, yield 83.3%). δH (400 MHz; (CD3)2CO; Me4Si): 10.62 (s, 1H), 9.16 (d, 1H, J=4.2 Hz), 8.94 (s, 0.58H) , 8.50 (dd, 1H, J1=8.5 Hz, J2=1.0 Hz), 8.11 (d, 1H, J=4.2 Hz), 7.71 (dd, 1H, J1=8.5 Hz, J2=7.8 Hz), 7.27 (dd, 1H, J1=7.8 Hz, J2=1.0 Hz).
References:
Wu, Shasha;Li, Shuixing;Li, Chang-Zhi;Shi, Minmin;Chen, Hongzheng [Tetrahedron Letters,2016,vol. 57,# 25,p. 2797 - 2799] Location in patent:supporting information
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