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ChemicalBook CAS DataBase List 2-MORPHOLIN-4-YL-QUINOLINE-3-CARBALDEHYDE
326008-62-2

2-MORPHOLIN-4-YL-QUINOLINE-3-CARBALDEHYDE synthesis

3synthesis methods
110-91-8 Synthesis
Morpholine

110-91-8
708 suppliers
$9.00/1g

73568-25-9 Synthesis
2-CHLOROQUINOLINE-3-CARBALDEHYDE

73568-25-9
193 suppliers
$9.00/250mg

-

Yield:326008-62-2 90%

Reaction Conditions:

with potassium carbonate in acetonitrile; for 15 h;Reflux;

Steps:

Synthesis of compound 2

2-chloro-3-formylquinoline (0.2 g, 1.04 mmol), K2CO3 (0.2 g, 1.57mmol), and dry CH3CN (10 mL) were added in a RB flask at roomtemperature. To this mixture, morpholine (0.09 g, 1.04 mmol) wasadded gradually in dropwise over 15 min. The reaction mixture was thenheated to reflux for 15 h and then cooled to room temperature. Afterremoval of solvent, the crude product was purified by silica gel columnchromatography by elution with hexane/ethyl acetate (3:1 v/v) toafford a yellow solid. Yield: 90%, Mp: 192 C. 1H NMR (CDCl3, 200MHz): δ (ppm): 10.12 (s, 1H), 8.42 (s, 1H), 7.66-7.70 (d, 1H), 7.26 (s,1H), 7.16-7.17 (d, 1H), 7.01-7.06 (dd, 1H), 3.90-3.96 (m, 4H),3.47-3.51 (m, 4H). 13C NMR (CDCl3, 100 MHz): δ (ppm): 51.46, 66.84,122.08, 124.15, 124.85, 127.63, 129.23, 132.61, 143.18, 149.32,158.84, 189.97.

References:

Velmurugan;Vickram;Jipsa;Karthick;Prabakaran;Suresh;Prabhu;Velraj;Tang;Nandhakumar [Food Chemistry,2021,vol. 348,art. no. 129098]