Hydrochloric Acid → 3-Chloro-4-(methoxycarbonyl)benzoic acid

To 3-amino-4-methoxycarbonylbenzoic acid (0.98 g, 5 mmol) suspended in 12 M hydrochloric acid (25 mL) and acetic acid (25 mL), an aqueous solution (10 mL) sodium nitrite (0.35 g, 5 mmol) was added at −10° C., and the resulting solution was stirred for 30 minutes. The solution was added to copper chloride (I) (0.99 g, 10 mmol) in 12 M hydrochloric acid (25 mL) at −10° C., and the resulting reaction mixture was stirred at room temperature for 1 hour. After addition of ethyl acetate, the reaction mixture was washed with water, dried over magnesium sulfate, filtered through celite and purified by silica gel column chromatography to give 0.44 g of the desired product as a colorless solid (yield 39%).

1. customthe resulting reaction mixture
2. stirringwas stirred at room temperature for 1 hour
3. washthe reaction mixture was washed with water
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered through celite
6. custompurified by silica gel column chromatography

ORD record

ord-f79d40d329954ea5807c145c067dea03

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318796B2