Reaction #64590

Reaction equation

hydrochloric acid

chloride

THF

Anthranilic acid

pyridine

tetrahydrofuran

→

N-n-octanoylanthranilic acid

Yield 79.4%

Conditions

Workup

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   FiltrationPyridine hydrochloride was filtered
3. 3
   Otherthe solvent was removed

Procedure

Anthranilic acid was dissolved in a mixed solvent containing pyridine and tetrahydrofuran (THF) in 5:5 ratio and a THF solution of n-caprioyl chloride was dropped to the solution during several hours for reaction. After the reaction, hydrochloric acid was added to the reaction mixture. Pyridine hydrochloride was filtered and the solvent was removed. N-n-octanoylanthranilic acid was obtained from the remaining reactant after the purification by column chromatography with the yield of 79.4%.

Source