Methanol → 3-(5-Methylpyridin-2-yl)-5-(pyrrolidine-1-carbonyl)benzoic acid

Participants

Reaction Steps

Into a round-bottom flask were charged methyl 3-(5-methylpyridin-2-yl)-5-(pyrrolidine-1-carbonyl)benzoate (0.80 g, 2.47 mmol), methanol (40 mL), sodium hydroxide (0.20 g, 5.0 mmol) and water (10 mL). The mixture was stirred at room temperature for 1 h. The volatiles were removed under reduced pressure. The residue was treated with 1N HCl (10 mL), concentrated, and purified via preparative HPLC to afford the desired product. LC-MS: 311.5 [M+1]+; 1H NMR (400 MHz, DMSO-d6): 8.61 (t, J=1.7 Hz, 1H), 8.52 (t, J=0.8 Hz, 1H), 8.16 (t, J=1.8 Hz, 1H), 7.99 (t, J=1.5 Hz, 1H), 7.80 (d, J=8.2 Hz, 1H), 7.72-7.69 (m, 1H), 3.50 (t, J=6.7 Hz, 2H), 3.41 (t, J=6.5 Hz, 2H), 2.35 (s, 3H), 1.91-1.81 (m, 4H).

Provenance & Evidence