2-(3,5-Bis-trifluoromethyl-benzoylamino)-4-nitro-benzoic acid methyl ester → 4-Amino-2-(3,5-bis-trifluoromethyl-benzoylamino)-benzoic acid methyl ester

Participants

Reaction Steps

To a solution of 2-(3,5-bis-trifluoromethyl-benzoylamino)-4-nitro-benzoic acid methyl ester (1.85 g, 4.24 mmol) in ethyl acetate (250 mL) in a Parr flask was added 10% palladium on carbon (0.20 g). The flask was attached to a Parr shaker and purged with nitrogen gas. The flask was then charged to 50 psi with hydrogen gas and the shaker was activated. After 2 hours the apparatus was recharged to 50 psi with hydrogen gas and the mixture was allowed to agitate. After an additional 2 hours the apparatus was recharged to 50 psi with hydrogen gas and the mixture was allowed to agitate for 4 additional hours (8 hours total time). The mixture was removed from the apparatus and filtered through a plug of Celite. The Celite was rinsed with ethyl acetate until no more color came through and the filtrate was concentrated under reduced pressure. The crude material was dissolved in ethyl acetate, dried over MgSO4, filtered and concentrated under reduced pressure to give 4-amino-2-(3,5-bis-trifluoromethyl-benzoylamino)-benzoic acid methyl ester (1.70 g, 99%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6); δ 13.52 (s, 1H), 8.49 (s, 2H), 8.44 (s, 1H), 7.83 (d, 1H), 7.73 (d, 1H), 6.40-6.36 (m, 2H), 6.37 (s, 2H), 6.36 (dd, 1H), 3.80 (s, 3H).

Provenance & Evidence