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 mixture was concentrated in vacuo and the resulting residue was dissolved in water (100 ml) and then acidifed 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, δH 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 mixture was concentrated in vacuo
2. dissolutionthe resulting residue was dissolved in water (100 ml)
3. additionacidifed 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-c6f332711d6b4ac1a725898ae8996f38

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247436B2