Yield:14132-96-8 71%

Reaction Conditions:

with hydrogenchloride in water; for 32 h;

Steps:

4.1.6 4-(4,5-Dibromo-6-oxopyridazin-1(6H)-yl)benzonitrile (46) (Scheme 1C)

General procedure: A suspension of 4-hydrazinylbenzonitrile hydrochloride (42) (9.360g, 55.19mmol, 1.25 equiv) in 6M HCl (220mL) was added to a solution/suspension of mucobromic acid (45) (11.430g, 44.32mmol, 1.00 equiv) in 6M HCl (300mL), and the resulting suspension was stirred at 65-95°C for 18h, when TLC analysis indicated the reaction was complete.²⁸ The viscous canary yellow suspension was cooled to 20°C and the solid was collected by filtration and washed sequentially with water and hexanes. The dried crude product was triturated with MeOH to furnish 46 (10.047g, 64%) as an amorphous off-white solid.

References:

Brooke, Darby G.;Van Dam, Ellen M.;Watts, Colin K.W.;Khoury, Amanda;Dziadek, Marie A.;Brooks, Hilary;Graham, Lisa-Jane K.;Flanagan, Jack U.;Denny, William A. [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 3,p. 1029 - 1039]