hydroxychloroquinoline

We repeated this work and we found that the o- and p-chloro derivatives were cyclized with equal ease under the conditions used previously (3) for the m-chloro derivative, giving almost quantitative conversion of the acrylates to 4-hydroxychloroquinoline-3-carboxylic acids.

1949, Royston M. Roberts, “The Reaction of Diarylformamidines with Ethyl Malonate”, in Lyndon F. Small, editor, Journal of Organic Chemistry, volume XI, Baltimore, Md.: The Williams & Wilkins Company, pages 278–279

Chloroquine is available as the phosphate (Avlochlor), and as the sulphate (Nivaquine). The drug is usually given orally, but may be given by slow intramuscular or intravenous injection for the emergency treatment of the acute attack. Hydroxychloroquinoline (Plaquenil) has similar properties.

1964 January 4, S. J. Hopkins, “Chemotherapy of Malaria: […]”, in The Chemist and Druggist, volume 181, number 4377, London: Allen & Hanburys Ltd, section “Therapeutic Treatment”, entry “Chloroquine”, page 12, column 2

[Use of hydroxychloroquinoline in the treatment of diarrheas of varied etiology] Bernades P. / Sem Hop Paris 41:1699-702, 8 Jun 65 (Fr)

1966, “Diarrhea”, in Cumulated Index Medicus, volume 7, part 1, “Subject Index D - M”, U.S. Department of Health, Education, and Welfare, section “Drug Therapy”, page S-1144, column 2

The introduction of the chlorine atom in 4-position, so as to obtain the desired dichloroquinolines of the above formula was most commonly effected by reacting phosphorus oxychloride with the corresponding 4-hydroxychloroquinoline, that is, a molecule having already a tertiary endocyclic nitrogen (see for example for these processes: J.A.C.S. 68 (1946) p. 113, 1204; J.A.C.S. 71 (1949) p. 1901; J.A.C.S. 73 (1951) p. 3168; J.A.C.S. 74 (1952) p. 5889; Chem. Ber. (1958) p. 499, etc.).

1971 March 2, “The Prior Art”, in Process for the Preparation of Chlorinated Quinolines, US Patent 3,567,732 (PDF version), page 1

One of these is an ester group whose saponification gives an acid, which is decarboxylated to give a hydroxychloroquinoline (5).

1989, Bryan G. Reuben, Harold A. Wittcoff, Pharmaceutical Chemicals in Perspective, John Wiley & Sons, Inc., →ISBN, page 408