Ammonia → HCID 68276549, compound

Participants

Reaction Steps

To a solution of 2-amino-5-fluoro-3-methyl-benzoic acid (4.80 g, 28.4 mmol) in THF (60 ml) is added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (10.9 g, 56.8 mmol), 1-hydroxybenzotriazole hydrate (4.34 g, 28.4 mmol) and ammonia as 5 M solution in dioxane (283 ml, 142 mmol). The resulting slurry is stirred for 3 hours. The reaction mixture is filtered through Celite and washed with THF. The filtrate is evaporated and partitioned between water and ethyl acetate. The organic phase is dried over sodium sulfate and evaporated. The residue is crystallized from 2-propanol to afford 2-amino-5-fluoro-3-methyl-benzamide as beige crystals; HPLC/MS 1.68 min (B), [M+H] 169.

Provenance & Evidence