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

Participants

Reaction Steps

To 2-amino-3-methylbenzoic acid (1.5 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 diisopropylethylamine (7.5 ml, 42 mmol). The mixture was purged with N2 and stirred for 60 h. The mixture was poured into water and extracte with EtOAc (50 mL×3), and the combined extracts were washed with brine (20 mL×2), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was dissolved in DCM and purified by silica gel chromatography eluting with 1:1 EtOAc/hexanes to afford 2-amino-3-methyl-benzamide as a white solid (1.3 g, 87%).

Provenance & Evidence