Anthranilic Acid → 2-(4-Chloro-2-nitroanilino)benzoic acid

HRID 16188

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12]([OH:21])(=[O:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH2:15].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(O)CCCC.[Cu].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[C:12]([OH:21])=[O:20])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

A solution of 4-chloro-1-fluoro-2-nitrobenzene (20 g, 114 mmol) and anthranilic acid (17.4 g, 127 mmol) in pentanol (250 mL) was heated to 120° C. in a Dean-Stark apparatus. Copper (126 mg, 2 mmol) was added, followed by potassium carbonate (12.7 g, 92 mmol). The resulting reaction mixture was stirred at 120° C. for 0.5 h and at 140° C. for 2 h. Subsequently, water and 1N (aq.) NaOH were added to dissolve the product. Then, the pH was adjusted to pH 5 and the water layer was extracted with ethyl acetate (3×). The combined organic layers were washed with water and brine, dried and evaporated. Ethanol was added to the obtained product. The title compound (14.4 g, 43%) was collected by filtration of the ethanol mixture.

Aufarbeitung

customThe resulting reaction mixture
dissolutionto dissolve the product
extractionthe water layer was extracted with ethyl acetate (3×)
washThe combined organic layers were washed with water and brine
customdried
customevaporated
additionEthanol was added to the obtained product
filtrationThe title compound (14.4 g, 43%) was collected by filtration of the ethanol mixture

Quellen und Nachweise

ORD-Eintrag: ord-d3c13c07f87242a2ae82606b819cd6b5
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07737136B2

Verknüpfte Notizen

Wird geladen…