Réaction #1244296

Équation de réaction

N,N-dipropyl-4-methyl-3-nitrobenzamide

hydrochloric acid

→

wa xy solid

Rendement 98.5%

N,N-dipropyl-3-amino-4-methylbenzamide

Rendement 98.5%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Autrequenched into water (500 mL)
2. 2
   workup.ADDITIONby addition of aqueous potassium hydroxide
3. 3
   workup.STIRRINGThe resulting pudding-like slurry was stirred with ethyl acetate (300 mL)
4. 4
   Filtrationfiltered (slow)
5. 5
   SéchageThe organic layer of the filtrate was dried (K2CO3)
6. 6
   Autreevaporated to a thick oil that solidified overnight

Mode opératoire

Crude N,N-dipropyl-4-methyl-3-nitrobenzamide (16.35 g, nominally 61.9 mmol) was dissolved in ethanol (125 mL). To this solution was added iron powder (11.34 g, 200 mmol), then, with rapid stirring, was added 12N hydrochloric acid (42 mL) at such a rate as to maintain a temperature of 75° C. (required 10 minutes). The solution was stirred at 75° C. for an additional 10 minutes, then quenched into water (500 mL). This slurry was made basic (pH 14) by addition of aqueous potassium hydroxide. The resulting pudding-like slurry was stirred with ethyl acetate (300 mL) and filtered (slow). The organic layer of the filtrate was dried (K2CO3) and evaporated to a thick oil that solidified overnight to provide 14.27 g (98.5%) of a wa xy solid that was characterized by proton nmr.

Source