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 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 reaction 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-0a74898941034ab9a7c3d2bec21ce7ff

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056867B2