Реакция #9575

Уравнение реакции

hydrochloric acid

Diethyl malonate

2-bromoaniline

sodium carbonate

→

N-(2-bromophenyl)malonamic acid

Выход 57.3%

Растворители

methanol

water

Условия реакции

Обработка

1. 1
   Другоеto collect the volatiles
2. 2
   Температураto cool to ambient temperature overnight
3. 3
   Другоеa precipitate formed
4. 4
   ДругоеThe precipitate was isolated by filtration
5. 5
   ТемператураThe mixture was heated
6. 6
   Температураat reflux for two hours
7. 7
   Температураto cool to ambient temperature
8. 8
   Температураcooled to 0° C
9. 9
   Другоеa white precipitate formed
10. 10
    ДругоеThe precipitate was isolated by filtration
11. 11
    Промывкаwashed with water
12. 12
    Другоеdried overnight on the filter funnel

Методика

Diethyl malonate (101 mL, 0.989 mol) and 2-bromoaniline (50.g, 0.291 mol) were combined and heated at 180° C. for six hours. A Dean-Stark trap was used to collect the volatiles. The reaction was allowed to cool to ambient temperature overnight; a precipitate formed. The precipitate was isolated by filtration and combined with methanol (160 mL), water (800 mL), and solid sodium carbonate (105 g). The mixture was heated at reflux for two hours, allowed to cool to ambient temperature, and then cooled to 0° C. The mixture was adjusted to pH 2 with the addition of 3 N hydrochloric acid; a white precipitate formed. The precipitate was isolated by filtration, washed with water, and dried overnight on the filter funnel to provide 43 g of N-(2-bromophenyl)malonamic acid as a white solid.

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