Sodium Cyanate → HCID 14626170, compound

Participants

Reaction Steps

To a solution of 4-amino-3-(diethylcarbamyloxy)-6,7-dimethoxy-1-methylisoquinoline (1.0 g, 3 mmol) in acetic acid (10 mL) was added sodium cyanate (0.23 g, 3.6 mmol) and the mixture was stirred under nitrogen at room temperature for 72 hours. Then the mixture was evaporated to dryness in vacuo and the residue triturated with water to give a gelatinous precipitate which was collected (0.69 g). The filtrate gave additional solids (0.50 g). The combined solids were dissolved in chloroform and purified by low pressure column chromatography on a silica gel column. Elution with 1.8% methanol/chloroform gave purified title compound which was collected from methylene chloride/ether as a colorless crystalline solid (0.865 g, 68.7%), mp 215°-216° C. IR (KBr): 3323, 3316, 3313, 3199, 1712, 1697, 1667, 1428 cm-1 ; NMR (CDCl3): δ 1.23 and 1.28 [each t, J=7 Hz, total 6H, N(CH2CH3)2 ], 2.80 (s, 3H, 1-CH3), 3.20-3.70 [br m, 4H, N(CH2CH3)2 ], 4.98 (s, 2H, NHCONH2), 6.78 and 7.01 (two s, each 1H, 5,8-H), 6.876 (br s, 1H, 4-NH). MS (DCI): 377 (MH)+ ; UV (EtOH) nm: 247 (ε51600), 275 (ε4800), 287 (ε5050), 297 (ε5000).

Provenance & Evidence