Ethanol → 3-Methyl-2-(nitromethylene)pyrrolidine

Participants

Reaction Steps

A solution of 12.7 grams (0.10 mole) of the ethyl imidate of 3-methyl-2-pyrrolidone in 30 milliliters of nitromethane was refluxed for four days with occasional distillation of ethanol by-product to bring the reflux temperature back to 100°C. Excess nitromethane (and ethanol present) then was evaporated under reduced pressure to give a dark oily residue. The residue was dissolved in ethyl acetate and passed through a Florisil column. Evaporation of the solvent from the filtrate left a crystalline residue, which when recrystallized from ether, gave 4.6 grams of 3-methyl-2-(nitromethylene)pyrrolidine, as a white solid, melting point: 47- 47.5°C.

Provenance & Evidence