Реакция #2048

Уравнение реакции

5-(N-acetylamino)acenaphthene

5-(N-acetylamino)acenaphthene

potassium hydroxide

p-iodo toluene

potassium carbonate

nitrobenzene

→

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

Выход 72.3%

Растворители

isoamyl alcohol

water

water

Условия реакции

Обработка

1. 1
   ДругоеTo 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
   Другоеthe toluene layer was separated
8. 8
   ПромывкаThe toluene layer was washed with 100 ml of water
9. 9
   Концентрированиеwas concentrated
10. 10
    ДругоеAn oily product thus obtained
11. 11
    Другоеwas purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4)

Методика

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.

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