Hydrochloric Acid → HCID 89825661, compound

Participants

Reaction Conditions

Reaction Steps

(E)-2-Amino-N′-(2-bromo-5-fluorophenyl)-2-oxoacetohydrazonoyl cyanide (10 g, 35 mmol), AlCl3 (20 g, 4.0 eq), and toluene (200 mL) were stirred at 120° C. overnight under N2. The reaction mixture was subsequently cooled to 0° C. and 2N HCl (200 mL) was added. The reaction mixture was stirred at 0° C. for 10 minutes and then filtered to afford a crude solid (4.5 g), which was dispersed in EtOH (500 mL). The mixture was stirred at RT for 4 hours and filtered. The filtrate was concentrated to give the title compound (1.5 g, 15%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.72 (1H, s), 8.62 (1H, s), 8.23-8.20 (1H, m), 8.00 (1H, s), 7.80 (1H, s), 7.47-7.42 (1H, m); LC-MS (5-95% ACN in H2O gradient with 0.02% NH4OAc, tR 3.020 minutes) ESI+APCI m/z [M+H]+ 285.

Provenance & Evidence