Lithium Hydroxide → 6-(5-Fluoro-2-hydroxyphenyl)nicotinic acid

Temperature

0 °C

methyl 6-(5-fluoro-2-hydroxyphenyl)nicotinate (1.47 g, 6.0 mmol) was dissolved in MeOH (35 ml) and cooled to 0° C. Lithium hydroxide (0.71 g, 30.0 mmol) was then added and the mixture stirred at 0° C. for 0.5 h. The mixture was then allowed to warm to room temperature. Additional lithium hydroxide (0.43 g, 18.0 mmol) was added and the allowed to stir at room temperature for 72 h. The mixture was then concentrated in vacuo and the resulting yellow solid dissolved in water (150 ml). Acidified to pH 1 by addition of 1 N aqueous HCl and the resulting precipitate was filtered and washed with 0.5 M aqueous HCl to afford the title compound as a yellow powder (1.15 g) (72%). 1H NMR (400 MHz, DMSO-d6) □ ppm 9.11 (1H, s), 8.42-8.28 (2H, m) 7.94-7.84 (1H, m), 7.26-7.15 (1H, m), 7.02-6.92 (1H, m). LRMS: ES m/z 234 [M+H]+.

1. temperatureto warm to room temperature
2. stirringto stir at room temperature for 72 h
3. concentrationThe mixture was then concentrated in vacuo
4. dissolutionthe resulting yellow solid dissolved in water (150 ml)
5. additionAcidified to pH 1 by addition of 1 N aqueous HCl
6. filtrationthe resulting precipitate was filtered
7. washwashed with 0.5 M aqueous HCl

ORD record

ord-397b721cf2c24fe5a97c4b6d7c6a8019

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902373B2