Reaktion #9575

Reaktionsgleichung

hydrochloric acid

Diethyl malonate

2-bromoaniline

sodium carbonate

→

N-(2-bromophenyl)malonamic acid

Ausbeute 57.3%

Lösungsmittel

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto collect the volatiles
2. 2
   Temperaturto cool to ambient temperature overnight
3. 3
   Sonstigea precipitate formed
4. 4
   SonstigeThe precipitate was isolated by filtration
5. 5
   TemperaturThe mixture was heated
6. 6
   Temperaturat reflux for two hours
7. 7
   Temperaturto cool to ambient temperature
8. 8
   Temperaturcooled to 0° C
9. 9
   Sonstigea white precipitate formed
10. 10
    SonstigeThe precipitate was isolated by filtration
11. 11
    Waschenwashed with water
12. 12
    Sonstigedried overnight on the filter funnel

Vorschrift

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.

Quelle