Sodium Hydroxide → 3-Amino-6-bromo-5-(trifluoromethyl)picolinic acid

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Reaction Steps

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.40 g, 4.68 mmol) was suspended in MeOH (15 mL); Sodium hydroxide (2.0 M aqueous solution) (14.04 mL, 28.1 mmol) was added and the suspension was stirred at RT overnight. The reaction mixture was concentrated in vacuo and the resulting residue was dissolved in water (100 mL) and then acidified by the addition of 5.0M HCl(aq). The product was extracted into ethyl acetate (2×75 mL) and the combined organic extracts were washed with water (50 mL), brine (25 mL), dried (MgSO4) and concentrated in vacuo to afford the title product as a yellow solid. 1H-NMR: [400 MHz, DMSO-d6] δ 13.24 (1H, br s, CO2H), 7.74 (1H, s, ArH), 7.17 92H, br s ArNH2). m/z 285.1, 287.1 [M+H]+

Provenance & Evidence