Pyridine → HCID 532191, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromobenzoic acid (5.02 g, 25.0 mmol) was sealed in a 250 mL flask with stir bar under nitrogen. Dichloromethane (72 mL) was then added and the solution was cooled on ice. Oxalyl chloride (2.19 ml, 25.0 mmol) and N,N-dimethylformamide (17 μL, 0.22 mmol) were added, and the reaction was removed from the ice bath and the resulting suspension was stirred for 20 h with a vent to an oil bubbler. After this time, the pale yellow solution was cooled on ice, then pyridine (4.04 ml, 50.0 mmol) and 3-nitroaniline (3.00 g, 21.7 mmol) were added. The reaction was then removed from the ice bath, and a water condenser was attached to the flask. The reaction was heated in an oil bath at 45° C., and after 1 h LC-MS analysis showed the reaction to be complete. The reaction was diluted with ethyl acetate (250 mL) and 1 M aqueous HCl (100 mL), then the layers were separated and the organic phase was washed again with aqueous HCl, then twice with half-saturated aqueous NaHCO3, then brine. The organics were dried over Na2SO4, filtered, and concentrated to a yellow solid, which was dried and pulverized several times, yielding the title compound (6.89 g, 99%). LRMS (ESI+) (M+H): 321.01.

Provenance & Evidence