Trifluoroacetic acid → 5-Cyano-3-methylpyridine-2-carboxylic acid

Participants

Reaction Steps

To a solution of tert-butyl 5-cyano-3-methylpicolinate (4.18 g, 19.15 mmol) in DCM (96 ml) was added TFA (148 ml, 1915 mmol), and the brown solution was stirred at RT for 2 h. The reaction mixture was concentrated. To the brown red residue was added EtOAc and it changed into a yellow slurry. It was concentrated again and dried on high vacuum. The reaction was triturated with 30 mL of MTBE and 50 ml of hexanes to yield 5-cyano-3-methylpicolinic acid (2.91 g, 17.95 mmol, 94% yield) as yellow solid. MS m/z=163.2 (M+H).

Provenance & Evidence