Pyridine → 4-[(8-Bromooctanoyl)amino]benzamide

Participants

Reaction Conditions

Reaction Steps

Pyridine (1.6 mL, 1.1 equivalents) is added to a mixture of 4-aminobenzamide (2.5 g, 18 mmol) and n-butyronitrile (65 mL) at 20° C. under an atmosphere of nitrogen. The mixture is stirred for 15 minutes before a solution of 8-bromooctanoyl chloride (3.7M in toluene, 5.5 mL, 20 mmol, 1.1 equivalents) in n-butyronitrile (10 mL) is added over 20 minutes. The mixture is then stirred at 20° C. for 22 hours. Upon complete reaction the mixture is filtered. The resulting product is washed with methanol (10 mL), water (2×25 mL), methanol (10 mL) and tert-butyl methyl ether (TBME, 10 mL) before being dried in vacuo to yield the title compound, generally as a solid.

Provenance & Evidence