Nitric Acid → 2-(4-Nitrobenzyl)-1-methylpyrrolidine

Reaktionsgleichung

[CH2:1]([CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15].[OH-].[Na+]>S(=O)(=O)(O)O>[N+:14]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH3:13])=[CH:3][CH:4]=1)([O-:16])=[O:15]

Komponenten

Versuchsvorschrift

Dissolve 27.9 g of 2-benzyl-1-methylpyrrolidine in 130 ml of conc. sulfuric acid, and add 100 ml of conc. nitric acid dropwise at 0°, with stirring, to the resulting solution. Continue stirring for a further 30 minutes at room temperature. Pour the mixture into 1 liter of ice water and alkalize with sodium hydroxide solution, with cooling. Extract the thus-produced preparation 4 times with, in each case, 150 ml of diethyl ether. Dry the ether phase over sodium sulfate and concentrate it to a red oil to obtain the title compound at a yield of 33.8 g (96% of theory). The hydrogen fumarate (from isopropanol) melts at 145° to 146°.