Chlorobenzene → HCID 69905525, compound

Participants

Reaction Steps

(E)-2-Amino-N′-(2-bromophenyl)-2-oxoacetohydrazonoyl cyanide (50.1 g, 187.5 mmol), AlCl3 (100 g, 750 mmol), and chlorobenzene (419 mL, 412 mol) were stirred at 115° C. overnight under N2. The reaction mixture was subsequently cooled to RT and 2M HCl (820 mL) was slowly added. The reaction mixture was stirred at 100° C. for 1 hour and then cooled. The product was collected by vacuum filtration, rinsed with EtOH (200 mL) and Et2O (100 mL), and dried under high vacuum to give an HCl salt of the title compound as a yellow solid (31.25 g, 62.5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.91 (1H, s), 9.43 (1H, s), 8.61-8.59 (1H, d, J=8.4 Hz), 8.43 (1H, s), 8.32-8.30 (1H, d, J=7.6 Hz), 7.94 (1H, s), 7.69-7.65 (1H, m); LC-MS (5-95% ACN in H2O gradient with 0.02% NH4OAc, tR 2.659 minutes) ESI+APCI m/z [M+H]+ 267.

Provenance & Evidence