Cyanamide → HCID 24741535, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-ethoxy-2-nitroaniline (15) (1.63 g, 9.0 mmol) and cyanamide (1.50 g, 35.8 mmol) were mixed together at 100° C., cooled to 50° C., cHCl (15 mL) added carefully and the mixture heated at 100° C. for 4 h. The mixture was cooled to 50° C., 7.5 M NaOH solution added until the mixture was strongly basic and the mixture stirred at 100° C. for 3 h. The mixture was cooled, diluted with water (100 mL), filtered, washed with water (3×20 mL), washed with ether (3×5 mL) and dried. The residue was purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give amine 16 (1.26 g, 68%) as a yellow powder, mp (MeOH) 268-271° C.; 1H NMR [(CD3)2SO] δ 8.02 (d, J=9.4 Hz, 1 H, H-8), 7.19 (brs, 2 H, NH2), 6.92 (dd, J=9.4, 2.6 Hz, 1 H, H-7), 6.83 (d, J=2.6 Hz, 1 H, H-5), 4.17 (q, J=7.0 Hz, 2 H, CH2O), 1.37 (t, J=7.0 Hz, 3 H, CH3); 13C NMR [(CD3)2SO] δ 163.9, 160.7, 151.2, 124.8, 121.4, 117.1, 104.2, 64.2, 14.1. Anal. Calcd for C9H10N4O2: C, 52.4; H, 4.9; N, 27.2. Found: C, 52.4; H, 4.8; N, 27.0%.

Provenance & Evidence