Water → HCID 15293175, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 8-(3-chlorophenyl)-1,6-naphthyridin-5-one (200 mg, 0.78 mmoles) and potassium carbonate (130 mg, 0.93 mmoles) in 10 ml DMF was added dropwise benzyl bromide (0.14 ml, 1.2 mmoles) under an atmosphere of nitrogen and stirred overnight at 21° C. The reaction mixture was poured into 100 ml water and after stirring for one hour the white precipitate was collected and dried. Crystallization from methanol gave 151 grams (56% yield) of the desired 6-benzyl-8-(3-chlorophenyl)-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 148.8°-150° C.; TLC in 1:4 EtOAc/Hex; 1H NMR (CDCl3, 300 MHz) δ5.28 (s, 2H), 7.30-7.55 (m, 10H), 8.78 (dd, 1H, J=8.1, 1.9), 8.94 (dd, 1H, J=4.5, 1.9); 13C NMR (75 MHz, CDCl3 ) δ154.31, 151.66, 136.97, 136.84, 136.17, 134.30, 134.13, 130.02, 129.51, 129.05, 128.23, 128.07, 127.77, 122.10, 122.01,119.86, 52.04; IR (KBr) vmax 1645, 1612, 1589, 1552, 1483, 1460, 1439, 1417, 1369, 1304, 1294, 1197, 1170, 790, 744, 729, 713, 702, 692, 599 cm-1 ; mass spectrum (EI), m/e 346. Anal. (C21H15ClN2O) Calcd.: C, 72.73; H, 4.36; N, 8.08. Found: C, 72.61; H, 4.35; N, 8.14.

Provenance & Evidence