Methanol → Methyl 4-pyridin-3-ylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[pyridin-3-yl]-benzoic acid (2.2 g, 11 mmol) (reference example 17b) in methanol (33 mL) was added conc. H2SO4 (5 mL). The resulting solution was warmed to 60° C. and stirred at this temperature for 45 min. The reaction mixture was then allowed to cool to room temperature then poured into ice. The pH of the resulting solution was adjusted to 7 using a 10 M solution of NaOH. The product was then extracted into ethyl acetate. This solution was washed with brine, dried over MgSO4 and concentrated to give 1.74 g of the title compound as a tan solid. 1H NMR (CDCl3) d 3.96 (s, 3H), 7.40 (dd, J=8, 5 Hz, 1H), 7.66 (m, 2H), 7.93 (m, 1H), 8.15 (m, 2H), 8.65 (bs, 1H), 8.89 (bs, 1H). MS (EI) m/z 213 (M)+.

Provenance & Evidence