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The catalytic conversion of amines of the furan series into homologues of pyrrole

Summary

  1. 1.

    A comparative study of the hydrogenation of 1-furyl-2-methyl-aminopropane in the vapor phase at 300° on Os-C, Rh-C, and skeletal Pd-Al and Cu-Al catalysts is reported.

  2. 2.

    On all these catalysts the initial reaction was hydrogenolysis of the furan ring at the C-O bond not adjacent to the substituent. This led to the formation of 2-n-propyl-4-methylpyrrole (50–85%). The best catalyst for this conversion was skeletal Cu-Al (85%).

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Literature cited

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    I. F. Bel'skii and N. I. Shuikin, Dokl. AN SSSR,137, 331 (1961); Izv. AN SSSR, Otd. khim. n. 493 (1962).

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    N. I. Shuikin, I. F. Bel'skii, and Kh. M. Minachev, Zh. obshch. khimii,29, 2969 (1959).

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    N. I. Shuikin and I. F. Bel'skii, Dokl. AN SSSR,125, 345 (1959).

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    J. Bremner, F. Starkey, and D. Dowden, Brit. Pat. 596880 (1943); Chem. Abstr.42, 4203 (1948); J. D. Webb and G. T. Borcherdt, J. Amer. Chem. Soc.73, 752 (1951).

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    A. Hinz, G. Meyer, and G. Schücking, Ber.76, 676 (1943).

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    C. F. Winans, J. Amer. Chem. Soc.61, 3566 (1939).

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Shuikin, N.I., Bel'skii, I.F. & Skobtsova, G.E. The catalytic conversion of amines of the furan series into homologues of pyrrole. Russ Chem Bull 12, 340–341 (1963). https://doi.org/10.1007/BF00846411

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Keywords

  • Hydrogenation
  • Pyrrole
  • Furan
  • Vapor Phase
  • Initial Reaction