Water → HCID 53905636, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 8-(3-chlorophenyl)-1,6-naphthyridin-5-one (128 mg, 0.5 mmoles) and potassium carbonate (83 mg, 0.6 mmoles) in 10 ml DMF was added dropwise 2-iodopropane (0.075 ml, 0.75 mmoles) under an atmosphere of nitrogen and stirred overnight at 21° C. The reaction mixture was poured into 50 ml water and after stirring for one hour the white precipitate was collected and dried. Crystallization from methanol gave 60 mg (40% yield) of the desired 6-(2-propyl)-8-(3-chlorophenyl)-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 163.5°-164.5° C.; TLC 1:4 EtOAc/Hex; 1H NMR (CDCl3, 300 MHz) δ1.454 (d, 6H, J=6.8), 5.3 (m, 1H, J=6.8), 7.36-7.60 (m, 6H), 8.77 (dd, 1H, J=8.3, 1.7), 8.93 (dd, 1H, J=4.4, 1.7); 13C NMR (75 MHz, CDCl3) δ154.20, 151.13, 137.54, 136.85, 134.18, 129.99,129.55, 128.28, 127.69, 121.95, 119.70, 46.57, 21.87; IR (KBr) vmax 1647, 1614, 1591, 1566, 1552, 1487, 1468, 1441, 1419, 1400, 1388, 1273, 1242, 1182, 1170, 796, 783, 711, 700, 605 cm-1 ; mass spectrum (EI), m/e 298. Anal. (C17H15ClN2O) Calcd.: C, 68.34; H, 5.06; N, 9.38. Found: C, 68.25; H, 5.11; N, 9.38.

Provenance & Evidence