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Report | Regular issue | Vol 19, No. 5, 1982, pp.837-847
Published online, 1st January, 1970
DOI: 10.3987/R-1982-05-0837
1- and 2-Chloromorphine. Halogenation of Morphine meta to the Free Phenolic Hydroxyl Group

Bajrang Bali Singh, Ranjit Singh Chauhan, Kattigari Madhava Madyastha, Surendra P. Bhatnagar, Kenneth L. Kirk, and Ulrich Weiss

*Laboratory of Chemical Diseases, National Institute of Diabetes and Digestive and Kidney, National Institute of Health, Bethesda, MD 20892, U.S.A.

Abstract

Treatment of morphine in aqueous HCl at 70° with KIO3 yields a monochloromorphine, identified as 1-chloromorphine by spectroscopic means and by the fact that it, and its methyl ether 1-chlorocodeine, are different from 2-chloromorphine and 2-chlorocodeine prepared from 2-aminomorphine of unequivocally established structure. Formation of 1-chloromorphine and the previously known 1-bromomorphine involves entry of the halogen into the position meta to the free phenolic hydroxyl. Possible mechanistic interpretations of this unusual orientation are discussed.