7-(diethylaMino)-2-oxo-2H-chroMene-3-carbaldehyde synthesis
- Product Name:7-(diethylaMino)-2-oxo-2H-chroMene-3-carbaldehyde
- CAS Number:57597-64-5
- Molecular formula:C14H15NO3
- Molecular Weight:245.27
Yield:57597-64-5 75%
Reaction Conditions:
with piperidine;acetic acid in ethanol for 12 h;Reflux;Inert atmosphere;
Steps:
Synthesis of 7-(diethylamino)-3-formyl-coumarin
4-(Diethylamino)-2-hydroxybenzaldehyde (1.33 g,6.9 mmol), diethyl malonate (1.65 g, 10.35 mmol),piperidine (1.77 g, 20.8 mmol) and two drops of aceticacid were dissolved in 100 mL ethanol. The mixture wasrefluxed under N2 for 12 h, then, the solvent was distilled andthe crude product was purified by column chromatography,ethyl acetate:dichloromethane (EtOAc:CH2Cl2 = 1:4, v/v)on silica gel to obtain 7-(diethylamino)-3-formyl-coumarinas a yellow oil (2.18 g, yield 75%). 1H NMR (300 MHz,CDCl3) δ 1.38 (m, 4H, CH2), 1.53 (m, 6H, CH3), 6.82 (s,1H, Ph-H), 6.76 (s, 1H, Ph-H), 8.50 (s, 2H, Ph-H).
References:
Zhou, Chen;Zhang, Yinan;Liu, Heng [Journal of the Brazilian Chemical Society,2018,vol. 29,# 3,p. 457 - 462]
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