反应 #2048

反应方程式

5-(N-acetylamino)acenaphthene

5-(N-acetylamino)acenaphthene

potassium hydroxide

p-iodo toluene

potassium carbonate

nitrobenzene

→

5-[N-(4-tolyl)amino]acenaphthene

收率 72.3%

溶剂

isoamyl alcohol

water

water

反应条件

后处理

1. 1
   其他To the resultant reaction mixture
2. 2
   workup.ADDITIONwas added an aqueous solution
3. 3
   workup.ADDITIONwas added
4. 4
   workup.DISTILLATIONisoamyl alcohol and nitrobenzene were distilled off by azeotropic distillation
5. 5
   workup.ADDITION100 ml of toluene was then added to the remaining material
6. 6
   workup.DISSOLUTIONto dissolve the reaction product
7. 7
   其他the toluene layer was separated
8. 8
   洗涤The toluene layer was washed with 100 ml of water
9. 9
   浓缩was concentrated
10. 10
    其他An oily product thus obtained
11. 11
    其他was purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4)

实验过程

7.39 g (0.035 mol) of the above prepared 5-(N-acetylamino)acenaphthene was mixed with 10.91 g (0.05 mol) of p-iodo toluene, 0.32 g (0.005 mol) of copper powder, 5.52 g (0.04 mol) of anhydrous potassium carbonate and 10 ml of nitrobenzene, and the mixture was stirred at 200° C. for 6 hours. The reaction was determined to be finished when disappearance of 5-(N-acetylamino)acenaphthene was identified. To the resultant reaction mixture, was added an aqueous solution having 10 ml of isoamyl alcohol and 9.8 g (0.15 mol) of 85% potassium hydroxide dissolved in 10 ml of water, and the resultant mixture was subjected to hydrolysis reaction at 130°-140° C. for 4 hours. After identifying the end of the hydrolysis reaction, 100 ml of water was added thereto, and isoamyl alcohol and nitrobenzene were distilled off by azeotropic distillation. 100 ml of toluene was then added to the remaining material to dissolve the reaction product, and the toluene layer was separated. The toluene layer was washed with 100 ml of water, and was concentrated. An oily product thus obtained was purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4). As this result, 6.56 g (yield: 72.3%, melting point: 96.2°-96.8° C.) of 5-[N-(4-tolyl)amino]acenaphthene was obtained.

来源