Carbon Dioxide → 2-Chloro-5-methylnicotinic acid

Temperature

-78 °C

A 2.5M solution of butyllithium in hexane (9.4 mL, 23.5 mmol) was added to tetrahydrofuran (50 mL) and the mixture cooled to −78° C. The mixture was treated with 2,2,6,6-tetramethylpiperidine (4.4 mL, 26.0 mmol) and stirred at −78° C. for 30 minutes. The reaction mixture was then treated with 2-chloro-5-methylpyridine (3.00 g, 23.5 mmol) and stirred at −78° C. for a further 2.5 hours. The reaction mixture was poured into a beaker of dry ice and warmed to room temperature on a water bath, then extracted into water. The mixture was acidified with 2M hydrochloric acid, extracted into ether and washed with water (×2) and brine. The solution was dried over magnesium sulphate to yield the title product as a yellow solid, 1.65 g.

1. stirringstirred at −78° C. for a further 2.5 hours
2. temperaturewarmed to room temperature on a water bath
3. extractionextracted into water
4. extractionextracted into ether
5. washwashed with water (×2) and brine
6. dry with materialThe solution was dried over magnesium sulphate

ORD record

ord-1da7180b7edf4c748f56cd029cb1d0e8

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07056934B2