Pyridine → HCID 66621507, compound

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (10 mL) was added to 4-(pyridin-4-yl)benzoic acid (1.6 g, 8 mmol) and the mixture was stirred under reflux overnight. The solvent was evaporated under reduced pressure and the residue was dried in vacuum giving 4-(pyridin-3-yl)benzoyl chloride. To a solution of methyl 3-amino-2-hydroxybenzoate (1 g, 6 mmol) and pyridine (480 mg, 6 mmol) in toluene (50 mL) was added 4-(pyridin-3-yl)benzoyl chloride (1.3 g, 6 mmol) portion wise at 0° C. and then stirred at 70° C. for 4 h. The resulting mixture was extracted with ethyl acetate (100 mL×4), the organic phase was washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain methyl 2-hydroxy-3-(4-(pyridin-4-yl)benzamido)benzoate as yellow solid (1.5 g, yield 71%). 1H-NMR (400 MHz, CDCl3) δ 4.00 (s, 3H), 6.97-7.01 (t, J=8.2 Hz, 1H), 7.57-7.63 (m, 3H), 7.78-7.80 (d, J=8.0 Hz, 2H), 8.05-8.07 (d, J=8.8 Hz, 2H), 8.67-8.78 (m, 4H), 11.44 (s, 1H); LC-MS (ESI) m/z: 349 (M+1)+.

Provenance & Evidence