Synthesis of pyrrole-2-carbonitriles

Details Synthesis of pyrrole-2-carbonitriles Synthesis of pyrrole-2-carbonitriles

2008-07-15

2008-07-15

Saeed, Kamal A (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

11086061

ABSTRACT:
The instant invention concerns processes for the production of pyrrole-2-carbonitriles such as 1-methylpyrrole-2-carbonitrile. Such processes preferably comprise the steps of reacting a pyrrole with chlorosulfonyl isocyanate in the presence of a solvent and contacting the resulting product with a molar excess of an amide such as N,N-dimethylformamide. The product of this contacting step is then contacted with a molar excess of an organic base to produce a precipitate and a solution phase. The precipitate is then separated from the solution phase and the corresponding pyrrole-2-carbonitrile is isolated from the resulting solution phase.

REFERENCES:
patent: 5204332 (1993-04-01), Brown et al.
patent: 6492402 (2002-12-01), Lee et al.
Barnett, G. H. et al., “Pyrrole chemistry. XXI. Synthetic approaches to cyanopyrroles,”J. Can. Chem.1980, 58, 409-411.
Yoshida, K., “Regiospecific Anodic Cyanation of Pyrroles and Indoles,”J. Am. Chem. Soc.1977, 99, 6111-6113.
Yoshida, K., “Photosensitised Electron Transfer and Anodic Cyanation Reactions of Nitrogen Heterocyles,”J. Chem. Soc., Chem. Commun.1978, 1108-1109.
Saito, I. et al., “Trimethylsilyl Cyanide as a Trapping Agent for Dipolar Peroxide Intermediates,”J. Am. Chem. Soc.1985, 107, 5279-5280.
Tamura, Y. et al., “Cyanation using the Combined Reagent, Triphenylphosphine-Thiocyanogen (TPPT): A New General Route to Indole and Pyrrole Carbonitriles,”J. Chem. Soc., Perkin Trans. I1980, 1132-1135.
Anderson, H. J., “Pyrrole Chemistry. II. 2-Pyrrolecarbonitrile, 1-Methyl-2-Pyrrolecarbonitrile, and their Nitration Products,”Can. J. Chem.1959, 37, 2053-2058.
Chakrabarti, J. K. et al., “A New Route to Nitriles. Dehydration of Aldoximes using 2,4,6-Trichloro-s-triazine (Cyanuric Chloride),”J. Chem. Soc., Chem. Commun.1972, 1226-1227.
Mlochowski, J. et al., Oxidative Conversion of N,N-Dimethylhydrazones Derived from Aliphatic and Heteroaromatic Aldehydes into Nitriles with Hydrogen Peroxide or 3-Chloroperoxybenzoic Acid,J. Prakt. Chem.1994, 336, 467-469.
Fernández, R. et al., Simple and Efficient Conversion of N,N-Dimethylhydrazones and Aldehydes to Nitriles,Tetrahedron Lett.1993, 34(1), 141-144.
Brückner, C. et al. “The Reductive Coupling of 2-Cyanopyrroles: A Study Pertaining to the Mechanism of Formation of Porphocyanines,”Tetrahedron, 1998, 54, 2021-2030.
Capdevielle, P. et al., “Simple and Efficient Copper-Catalyzed One-Pot Conversion of Aldehydes into Nitriles,”Synthesis Communications, Jun. 1989, 451-452.
Wang, N-C. et al., “Pyrrole chemistry. XVII. Alkylation of the pyrrolyl ambident anion,”Can. J. Chem, 1977, 55, 4112-4116.
Loader, C. E. et al., “Pyrrole chemistry. XXIII. The cyanation of substituted pyrroles with chlorosulfonyl isocyanate (CSI). New syntheses of pyrrole-3-carbonitriles,”Canadian Journal of Chemistry, 1981, 59, 2673-2676.
Vorbrüggen, H., “Reaktive Isocyanate I. Die Direkte Einfuehrung Von Nitril-Gruppen in Ungesattigte Systeme. Eine Einfache Umwandlung Von Carbonsäuren in Ihre Nitrile,”Tetrahedron Letters, 1968, 9(13), 1631-1634.

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