반응 #44466

반응 방정식

NaOH

4-chloro-1-fluoro-2-nitrobenzene

anthranilic acid

potassium carbonate

→

2-[(4-Chloro-2-nitrophenyl)amino]benzoic Acid

용매

water

pentanol

반응 조건

후처리

1. 1
   기타The resulting reaction mixture
2. 2
   workup.DISSOLUTIONto dissolve the product
3. 3
   추출the water layer was extracted with ethyl acetate (3×)
4. 4
   세척The combined organic layers were washed with water and brine
5. 5
   기타dried
6. 6
   기타evaporated
7. 7
   workup.ADDITIONEthanol was added to the obtained product
8. 8
   여과The title compound (14.4 g, 43%) was collected by filtration of the ethanol mixture

실험 절차

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.

출처