Ammonia → HCID 9925679, compound

Participants

Reaction Steps

Ammonia gas was bubbled into a solution of 361 mg (1.12 mmol) of 4-(2-isopropoxy-3,4-dioxo-cyclobut-1-enyl)-2,2-dimethyl-2H-chromene-6-carbonitrile in acetonitrile (11 ml) for 30 min. The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was quenched with H2O (50 mL) and was extracted into 20% THF-CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4 and then concentrated and recrystallized from acetone-petroleum ether to give 110 mg of the title compound (35% yield), mp>250° C., as an off white solid: 1H-NMR (DMSO-d6 ; 400 MHz) δ9.18 (bs, 1H), 8.68 (bs, 1H), 7.79 (d, 1H), 7.67 (dd, 1H), 7.01 (d, 1H), 6.29 (s, 1H), and 1.47 ppm (s, 6H); IR (KBr) 3300, 3100, 1780, 1730, 1720, 1665, and 1610 cm-1 ; mass spectrum (PBEI), m/e 281 (M+H), 280 (M+), 252, and 209.

Provenance & Evidence