N,N-Dimethylethylenediamine → HCID 10545217, compound

Participants

Reaction Steps

7-Chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (1 g) and N,N-dimethylethylenediamine (30 ml) were heated in a sealed tube at 180° C. for 10 days. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and saturated potassium carbonate solution. The organic layer was separated, dried (Na2SO4) and the solvent was removed under vacuum. The residue was dissolved in HCl, washed with diethyl ether (2×), then basified with sodium hydroxide, extracted into ethyl acetate, dried (MgSO4), and concentrated in vacuo, to give 0.248 g of the title compound; mp 230° C. (ethyl acetate); Found: C, 63.76; H, 5.64; N, 11.75.C19H2O ClN3O.0.9H2O requires C, 63.37; H, 6.14; N, 11.76%. δ (360 MHz, DMSO-d6) 1.94 (6H, s, (CH3)2N), 2.17 (2H, m, NCH2CH2N), 2.69 (2H, m, NCH2CH2N), 5.82 (1H, br s, NH), 7.17-7.95 (8H, m, aromatics), 11.23 (1H, br s, NH); m/z (CI+) 341 (M+).

Provenance & Evidence