Reaktion #569712

Reaktionsgleichung

sodium hydrogencarbonate

N-methyl-4-acetoxy-2,3,5-trimethylaniline hydrochloride

nitric acid

→

title compound

N-Methyl-4-acetoxy-2,3,5-trimethyl-6-nitroaniline

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling, for 10 minutes
2. 2
   Extraktionafter which it was extracted with ethyl acetate
3. 3
   WaschenThe extract was washed with a saturated aqueous solution of sodium chloride
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   SonstigeThe solvent was then removed by distillation under reduced pressure
6. 6
   workup.ADDITIONafter which 50 ml of diisopropyl ether and 50 ml of hexane were added to the residue
7. 7
   workup.STIRRINGThe mixture was then agitated ultrasonically for 5 minutes
8. 8
   SonstigeInsoluble precipitates
9. 9
   Sonstigewere triturated with a 1:1 by volume mixture of diisopropyl ether and hexane
10. 10
    FiltrationThe resulting crystals were collected by filtration
11. 11
    Waschenafter which they were washed with a 1:1 by volume mixture of diisopropyl ether and hexane

Vorschrift

4.3 g of N-methyl-4-acetoxy-2,3,5-trimethylaniline hydrochloride [prepared as described in step (h) above] were added to ice-cooled concentrated aqueous nitric acid, and the resulting mixture was stirred, whilst ice-cooling, for 10 minutes and then at room temperature for 10 minutes. At the end of this time, the reaction mixture was poured into ice-water and the aqueous mixture was neutralized by the addition of sodium hydrogencarbonate, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, after which 50 ml of diisopropyl ether and 50 ml of hexane were added to the residue. The mixture was then agitated ultrasonically for 5 minutes. Insoluble precipitates were triturated with a 1:1 by volume mixture of diisopropyl ether and hexane. The resulting crystals were collected by filtration, after which they were washed with a 1:1 by volume mixture of diisopropyl ether and hexane to give 2.76 g of the title compound, melting at 143°-146° C.

Quelle