5-Fluoro-N-methyl-2-nitrobenzamide → 2-Amino-5-fluoro-N-methylbenzamide

Participants

Reaction Steps

A solution of 5-fluoro-N-methyl-2-nitrobenzamide (Compound 102B) in EtOH (10.0 mL) was charged with Palladium 10% wt on activated carbon (0.316 g, 0.297 mmol). The reaction mixture was evacuated and purged with hydrogen gas (3 times). The reaction mixture was allowed to stir under hydrogen at rt for 16 h. The reaction mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure to yield a light yellow semi-solid. The material was purified by silica gel chromatography using DCM/MeOH (100:0→95:5) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield a white solid, 0.500 g (100% yield). 1H NMR (CDCl3, 400 MHz): δ=2.98 (d, J=4.80 Hz, 3 H), 5.30 (d, J=5.31 Hz, 1 H), 6.64 (dd, J=8.84, 4.80 Hz, 1 H), 6.96 (ddd, J=8.91, 7.89, 2.91 Hz, 1 H), 7.02 (dd, J=9.22, 2.91 Hz, 1 H). MS (ES+): m/z 169.08 [MH+] (TOF, polar).

Provenance & Evidence