Potassium Nitrate → 6-Chloro-2-methyl-3-nitrobenzoic acid

2-Chloro-6-methylbenzoic acid (99 mg, 0.58 mmol) was dissolved in conc. hydrochloric acid (1 mL) and cooled in an ice bath. To this solution potassium nitrate in conc. hydrochloric acid (1 mL) was added drop wise. The reaction mixture was stirred for 5 min, then the ice bath was removed and stirring was continued for another 2 hours. The reaction mixture was poured onto ice (25 g) and extracted with ethyl acetate (3×25 mL). The combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo to give a mixture of the desired 3-nitro (70%) and the 5-nitro (30%) derivatives (118.6 mg, 95%). No effort was made to separate the two isomers, and the mixture was used in the next step.

1. temperaturecooled in an ice bath
2. customthe ice bath was removed
3. stirringstirring
4. waitwas continued for another 2 hours
5. additionThe reaction mixture was poured onto ice (25 g)
6. extractionextracted with ethyl acetate (3×25 mL)
7. dry with materialThe combined organic layers were dried over sodium sulphate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give
11. customto separate the two isomers

ORD record

ord-712b655f7aaf40abb887d894ebed7ab1

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07585877B2