Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 7
21
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of 2-Aminomorphine and 2-Aminocodeine. Reduction of Aromatic Nitro Groups with Formamidinesulfinic Acid

, &
Pages 647-657 | Received 19 Mar 1979, Published online: 06 Dec 2006

References

  • 10458 Bronx, N. Y. : Department of Chemistry, Fordham University .
  • Chatterjie , N. , Inturrisi , C. E. , Dayton , H. B. and Blumberg , H. 1975 . J. Med. Chem. , 18 : 490
  • Chatterjie , N. , Umans , J. G. and Inturrisi , C. E. 1976 . J. Org. Chem. , 41 : 3624
  • Chatterjie , N. , Umans , J. G. , Inturrisi , C. E. , Chen , W.-C. , Clarke , D. D. , Bhatnagar , S. P. and Weiss , U. 1978 . J. Org. Chem. , 43 : 1003
  • Brine , G. A. , Boldt , K. G. , Coleman , M. L. , Bradley , D. J. and Carroll , F. I. 1978 . J. Org. Chem. , 43 : 1555
  • Bognar , R. and Gaal , G. D. 1963 . Magy. Kem. Foly. , 69 : 17 Chem. Abstr., 59, 1696b (1963)
  • Ochiai , E. and Nakamura , T. 1939 . Chem. Ber. , 72 : 684
  • Aoki , M. , Kusama , T. , Kuboyama , N. and Murakoshi , Y. 1974 . Nippon Daigaku Kenkyu Hokoku , 14 : 8 Chem. Abstr., 84, 12640f (1976)
  • Takagi , S. , Tanaka , H. and Yokoyama , A. 1957 . Chem. Pharm. Bull. (Japan) , 5 : 615
  • Gore , P. H. 1954 . Chem. and Ind. , : 1355
  • Okuda , S. , Yamaguchi , S. , Kawazoe , Y. and Tsuda , K. 1964 . Chem. Pharm. Bull. , 12 : 104 T. J. Batterham, K. H. Bell, and U. Weiss, Austral. J. Chem., 18, 1799 (1965)
  • Fishman , J. , Norton , B. , Cotter , M. and Hahn , E. F. 1974 . J. Med. Chem. , 17 : 778
  • Degraw , J. I. , Lawson , J. A. , Crase , J. L. , Johnson , H. L. , Ellis , M. , Uyeno , E. T. , Loew , G. H. and Berkowitz , D. S. 1978 . J. Med. Chem. , 21 : 415
  • Iijama , I. , Minamikawa , J.-I. , Jacobson , A. E. , Brossi , A. and Rice , K. C. 1978 . J. Org. Chem. , 43 : 1462 and references cited therein
  • Liebman , A. A. , Malarek , D. H. , Blount , J. F. , Nelson , N. R. and Delaney , C. M. 1978 . J. Org. Chem. , 43 : 737
  • Cone , E. J. , Gorodetzky , C. W. , Darwin , W. D. , Carroll , F. I. , Brine , G. A. and Welch , C. D. 1978 . Research Communications in Chemical Pathology and Pharmacology Vol. 20 , 413
  • Wieland , H. and Kappelmeier , P. 1911 . Justus Liebig's Ann. , 382 : 306 these authors formulated the compound as 2-nitrosomorphine; it was subsequently identified as 2-nitromorphine by Ochiai and Nakamura7
  • This substance crystallized with one molecule of water as evidenced by elemental analysis; the analysis reported by Weiland and Kappelmeier also was for a monohydrate of the free base 1c 17
  • A two molar excess of NaOH over FSA was found to be satisfactory in all these reductions of the nitro compounds

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.