1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Amino-3-fluorobenzamide

Participants

Reaction Steps

To 2-amino-3-fluorobenzoic acid (1.55 g, 10 mmol) in DMF (5 mL) at rt were added hydroxybenzatriazole (2.0 g, 13 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.3 g, 12 mmol), ammonium chloride (2.3 g, 42 mmol), and DIEA (7.5 ml, 42 mmol). The mixture was purged with nitrogen and stirred for 6 h. The mixture was then poured into water and extracted with EtOAc (3×50 mL). The combined extracts were washed with brine (2×20 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was treated with DCM (10 mL) resulting in a precipitate that was collected by filtration to afford 2-amino-3-fluorobenzamide (670 mg). LC-MS (ESI) m/z 155 (M+H+)

Provenance & Evidence