4-Chloro-2-acetamidobenzoic acid → 2-Amino-4-chlorobenzoic acid
Reaction equation
C([NH:4][C:5]1[C:6](=[CH:10][CH:11]=[C:12]([Cl:14])[CH:13]=1)[C:7]([OH:9])=[O:8])(=O)C>Cl>[Cl:14][C:12]1[CH:13]=[C:5]([NH2:4])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
The damp N-acetyl-4-chloroanthranilic acid is suspended in 400 ml of concentrated hydrochloric acid (12M) and stirred and heated at 80° C. for 8 hours. The mixture is cooled to 10° C. and the resulting 4-chloroanthranilic acid hydrochloride is recovered by filtration. The solid is suspended in 300 ml water and sodium acetate is added, portionwise until the pH is 5. The resulting 4-chloroanthranilic acid is recovered by filtration and recrystallized from the minimum of hot ethanol. The final yield of off-white crystals was about 50 g, melting at about 239°-240° C.