Chemistry of Heterocyclic Compounds

, Volume 13, Issue 1, pp 54–58 | Cite as

Formation of isoindole derivatives by reaction of phthalonitrile with sodium methoxide

  • É. V. Pankratova
  • G. N. Rodionova
  • B. E. Zaitsev
  • V. A. Titkov


It is shown by means of IR spectra that the reaction of phthalonitrile with sodium methoxide in benzene in the presence of traces of water or methanol proceeds via a series-parallel mechanism in two steps to give cyclic products. The proposed structure of the intermediate is an oligomeric isbindolenine chain with terminal NNa and OCH3 groups. The final product is the sodium salt of monomethoxyiminoisoindolenine. The analogous reaction in methanol proceeds at a higher rate that makes it impossible to isolate or detect the intermediate; the final product is 1,1-dimethoxy-3-iminoisoindoline.


Sodium Methanol Benzene Organic Chemistry Methoxide 
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Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • É. V. Pankratova
    • 1
  • G. N. Rodionova
    • 1
  • B. E. Zaitsev
    • 1
  • V. A. Titkov
    • 1
  1. 1.Scientific-Research Institute of Organic Intermediates and DyesMoscow

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