Methanol → 2'-Cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid

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Reaction Steps

A round-bottom flask was charged with methyl 2′-cyano-4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate (0.17 g, 0.46 mmol), lithium hydroxide (17 mg, 0.70 mmol), methanol (5 mL), and water (1 mL). The mixture was stirred at room temperature overnight. The evolatiles were removed under reduced pressure and the residue was acidified with 1 N HCl, extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, concentrated to afford the desired product as a white solid. LC-MS: 335.4 [M+1]+; 1H NMR (400 MHz, DMSO-d6): 8.14 (t, J=1.6 Hz, 1H), 8.10 (t, J=1.5 Hz, 1H), 7.93 (t, J=1.7 Hz, 1H), 7.83 (t, J=0.8 Hz, 1H), 7.66-7.60 (m, 2H), 3.51-3.42 (m, 4H), 2.42 (s, 3H), 1.91-1.83 (m, 4H).

Provenance & Evidence