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

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]+

1. concentrationThe reaction mixture was concentrated in vacuo
2. dissolutionthe resulting residue was dissolved in water (100 mL)
3. additionacidified by the addition of 5.0M HCl(aq)
4. extractionThe product was extracted into ethyl acetate (2×75 mL)
5. washthe combined organic extracts were washed with water (50 mL), brine (25 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo

ORD record

ord-0593f2faa1d4420c99f61606f6f8edc2

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034879B2