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

Participants

Reaction Steps

To a solution of 5-cyano-3-methyl-pyridine-2-carboxylic acid tert-butyl ester (8.50 g, 38.9 mmol) in 1,3-dimethoxybenzene (51 ml, 389 mmol) was added TFA (85 ml) and stirred for 6.5 h. The reaction mixture was diluted with toluene and evaporated. The residue was taken up in toluene and evaporated (2×). The product was crystallized from TBME/hexanes to give the title compound as a white powder. HPLC: RtH1=2.314 min; ESIMS [M+Na]+=163; 1H-NMR (360 MHz, CDCl3): δ 8.77 (s, 1H), 8.07 (s, 1H), 2.87 (s, 3H).

Provenance & Evidence