Nitric Acid → 1-Acetyl-2-(4-nitrobenzyl)pyrrolidine

HRID 1278068Notes

Reaction equation

HRID 1278068 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[C:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 23452530HCID 23452530, compound

Product 1

HCID 160394911-Acetyl-2-(4-nitrobenzyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Dissolve 5.0 g of 1-acetyl-2-benzylpyrrolidine (at 0°) in 25 ml of concentrated sulfuric acid. At this temperature add (dropwise, with stirring) 20 ml of concentrated nitric acid to the thus-prepared solution. After warming the obtained reaction mixture to room temperature, pour it into 200 ml of ice water and extract it with diethyl ether. After drying over sodium sulfate, treat the extract with activated charcoal and then distil off the solvent to obtain the title compound as reddish oil.

Workup

  1. additionAt this temperature add (dropwise,
  2. temperatureAfter warming
  3. customthe obtained reaction mixture to room temperature
  4. extractionextract it with diethyl ether
  5. dry with materialAfter drying over sodium sulfate
  6. additiontreat the
  7. extractionextract with activated charcoal
  8. customdistil off the solvent

Sources & evidence

ORD record
ord-028fa41790264ecd9f3c7eef05d4c8d3
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

Loading…