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

HRID 1605689Notes

Reaction equation

HRID 1605689 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][NH:4][C:3]1=O.C(O)C.[O-][Si]([O-])=O.[Mg+2].[N+:16]([CH3:19])([O-:18])=[O:17]>C(OCC)(=O)C>[CH3:1][CH:2]1[CH2:6][CH2:5][NH:4][C:3]1=[CH:19][N+:16]([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 6375NitromethaneHCID 61680MAGNESIUM SILICATE (synthetic)HCID 1028483-Methylpyrrolidin-2-one

Product 1

HCID 704582543-Methyl-2-(nitromethylene)pyrrolidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. customback to 100°C
  2. customExcess nitromethane (and ethanol present) then was evaporated under reduced pressure
  3. customto give a dark oily residue
  4. customEvaporation of the solvent from the filtrate
  5. waitleft a crystalline residue, which when
  6. customrecrystallized from ether

Sources & evidence

ORD record
ord-1200379cad154733bce05ec1a6ae507e
Source dataset
uspto-grants-1976_04
Patent number
US03950530

Reaction notes

Loading…