Pyridine → 2-Bromo-N-(3-butyramidophenyl)benzamide

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Reaction Steps

2-Bromobenzoic acid (259 mg, 1.29 mmol) was sealed in a flask with stir bar under nitrogen, then dissolved with dichloromethane (7.5 mL) and cooled on ice. Oxalyl chloride (113 μL, 1.29 mmol) and N,N-dimethylformamide (4 μL, 0.06 mmol) were added, then the reaction was removed from the ice bath and stirred for 3 h with a vent to an oil bubbler. N-(3-Aminophenyl)butyramide (200 mg, 1.12 mmol) was then added, followed by pyridine (209 μL, 2.58 mmol). After 18 h, LC-MS analysis showed complete consumption of the amine reactant. The reaction was diluted with ethyl acetate (40 mL) and 1 M aqueous HCl (40 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 colorless oil. The oil was redissolved with dichloromethane, then hexane was added to induce the precipitation of an amorphous solid. The suspension was concentrated and dried under hi-vacuum to yield the title compound (382 mg, 94%). LRMS (ESI+) (M+H): 361.12.

Provenance & Evidence