Cyanamide → 8,9-Dihydro-7H-indeno[5,4-e][1,2,4]triazin-3-amine 1-Oxide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-nitro-5-indanamine (3) (0.67 g, 3.8 mmol) and cyanamide (0.63 g, 15.0 mmol) were mixed together at 100° C., cooled to 50° C., cHCl (5 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 (0-5%) of MeOH/DCM, to give amine 4 (279 mg, 37%) as a yellow powder: mp (MeOH/DCM) 270-274° C.; 1H NMR [(CD3)2SO] δ 7.56 (d, J=8.4 Hz, 1H, H-6), 7.31 (d, J=8.4 Hz, 1H, H-5), 6.79 (br s, 2H, NH2), 3.55 (br t, J=7.5 Hz, 2H, H-9), 2.95 (br t, J=7.7 Hz, 2H, H-7), 2.09-2.20 (m, 2H, H-8); 13C NMR [(CD3)2SO] δ 159.4, 148.7, 140.9, 136.0, 131.6, 128.1, 123.9, 34.6, 32.1, 24.1. Anal. calcd for C10H10N4O: C, 59.4; H, 5.0; N, 27.7. Found: C, 59.5; H, 5.0; N, 27.7%.

Provenance & Evidence