Reaktion #5958

Reaktionsgleichung

Compound ( f )

N-[4-(2-Carbomethoxyphenyl)benzyl]phthalimide

Hydrazine hydrate

→

pale yellow oil

Ausbeute 66.3%

4-(2-Carbomethoxyphenyl)benzylamine

Ausbeute 66.3%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith warming
2. 2
   TemperaturThe solution is heated
3. 3
   Temperaturto reflux for 10 minutes
4. 4
   Filtrationfiltered
5. 5
   WaschenThe precipitate is washed with excess hot ethanol

Vorschrift

Compound (f) of Example 6 (3.85 g, 0.01 mole) is dissolved in 100 mL of absolute ethanol with warming. Hydrazine hydrate (7.5 mL) is added at once. The solution is heated to reflux for 10 minutes and the reaction mixture sets up. The mixture is cooled to room temperature and filtered. The precipitate is washed with excess hot ethanol. The ethanol fraction is rotovapped to a pale yellow oil. Chromatography on silica gel using methylene chloride/25% methanol as the mobile phase yields 1.6 g (66%) of a pale yellow oil. 1H NMR (CDCl3) 7.83 (1H, d, J=7 Hz); 7.6-7.2 (7H, m); 3.92 (2H, s); 3.66 (3H, s); 2.16 (2H, bs). Mass Spec. (DCl) m/z 242 (M+H). Analysis--calc'd for C15H15NO2.H2O: C, 71.97; H, 6.44; N, 5.60; found: C, 71.60; H, 6.27; N, 5.70.

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