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

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Reaction Steps

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°.

Provenance & Evidence