Ammonium Acetate → HCID 19373031, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-(3-chlorophenyl)pyrano [3,4-b]pyridin-5-one (1.25 g., 4.9 mmoles) in 20 ml DMF was added solid ammonium acetate (0.56 g., 7.29 mmoles). The reaction was heated at 50° C. under nitrogen for one hour, cooled and concentrated under vacuum. The solid was triturated with ether to give 1.1 grams (88% yield) 8-(3-chlorophenyl)-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 252°-252.5° C.; 1H NMR (DMSO-d6, 300 MHz) δ7.37-7.66 (m, 6H), 8.58 (dd, 1H, J=8.2, 2.1), 8.94 (dd, 1H, J=4.69, 1.68), 11.85 (bs, 1H); 13C NMR (75 MHz, DMSO-d6) δ161.74, 154.04, 151.91, 137.69, 135.62, 132.47, 132.26, 129.68, 129.55, 128.43, 126.64, 121.85, 121.60, 116.87; IR (KBr) vmax 3437, 3173, 3032, 2951, 2878, 1672, 1630, 1593, 1566, 1477, 1462, 1417, 1340, 1236, 821, 794, 692, 671, 603, 555 cm-1 ; mass spectrum (EI), m/e 256. Anal. (C14H9ClN2O) Calcd.: C, 65.51; H, 3.53; N, 10.91; C1, 13.81. Found: C, 65.67; H, 3.34; N, 10.98; C1, 13.91.

Provenance & Evidence