4-Chloro-2-acetamidobenzoic acid → 2-Amino-4-chlorobenzoic acid

HRID 2379670

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

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.

Workup

temperatureThe mixture is cooled to 10° C.
filtrationthe resulting 4-chloroanthranilic acid hydrochloride is recovered by filtration
additionsodium acetate is added, portionwise until the pH is 5
filtrationThe resulting 4-chloroanthranilic acid is recovered by filtration
customrecrystallized from the minimum of hot ethanol

Sources & evidence

ORD record: ord-50e9b283033b4c4dabaa4c15d1720d64
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05364767

Linked notes

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