反応 #44466

反応方程式

NaOH

4-chloro-1-fluoro-2-nitrobenzene

anthranilic acid

potassium carbonate

→

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

溶媒

water

pentanol

反応条件

後処理

1. 1
   その他The resulting reaction mixture
2. 2
   workup.DISSOLUTIONto dissolve the product
3. 3
   抽出the water layer was extracted with ethyl acetate (3×)
4. 4
   洗浄The combined organic layers were washed with water and brine
5. 5
   その他dried
6. 6
   その他evaporated
7. 7
   workup.ADDITIONEthanol was added to the obtained product
8. 8
   ろ過The title compound (14.4 g, 43%) was collected by filtration of the ethanol mixture

実験手順

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.

出典