# hydroxychloroquinoline
## English
### Etymology

From hydroxy- +‎ chloroquinoline.

### Noun

hydroxychloroquinoline (uncountable)
* Synonym of hydroxychloroquine
** 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: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.
** 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: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.
** 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:[Use of hydroxychloroquinoline in the treatment of diarrheas of varied etiology] Bernades P. / Sem Hop Paris 41:1699-702, 8 Jun 65 (Fr)
** 1971 March 2, “The Prior Art”, in Process for the Preparation of Chlorinated Quinolines, US Patent 3,567,732 (PDF version), page 1: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.).
** 1973, Cerebral Vascular Diseases, American Heart Association, →ISBN, page 316, column 1:Hydroxychloroquinoline, affecting platelets, 292
** 1989, Bryan G. Reuben, Harold A. Wittcoff, Pharmaceutical Chemicals in Perspective, John Wiley & Sons, Inc., →ISBN, page 408:One of these is an ester group whose saponification gives an acid, which is decarboxylated to give a hydroxychloroquinoline (5).
** 2020, Sara Szymkuć, Ewa P. Gajewska, Karol Molga, Agnieszka Wołos, Rafał Roszak, Wiktor Beker, Martyna Moskal, Piotr Dittwald, Bartosz A. Grzybowski, “Computer-generated “synthetic contingency” plans at times of logistics and supply problems: scenarios for hydroxychloroquine and remdesivir”, in Chemical Science, Royal Society of Chemistry, section “Results and discussion”, subsection “Known syntheses of hydroxychloroquine (HCQ)”, page 6738, column 2:The heterocyclic part of HCQ, 1, is rather inexpensive (1.50 $ per g from S-A, 0.26 $ per g from Biosynth Carbosynth) and in case of supply problems, can be sourced (in 94% yield, via chlorination using POCl₃) from hydroxychloroquinoline 13 which, in turn, can be made in ~40% yields in two steps either from 3-chloroaniline, diethyl malonate and ethyl orthoformate (respectively, 9.51 $ per g from S-A, 0.05 $ per g from Oakwood Chemical, OC; 0.04 $ per g from S-A, 0.015 $ per g from OC; 0.12 $ per g from S-A, 0.03 $ per g from OC) or from 3-chloroaniline, acrylic acid (or methyl acrylate) and tosyl chloride (respectively, 9.51 $ per g from S-A, 0.05 $ per g from OC; 1.48 $ per g from S-A, 0.02 $ per g from Gelest Inc.; 1.43 $ per g from S-A, 0.03 $ per g from Alfa Aesar; 0.02 $ per g from S-A, 0.04 $ per g from Alfa Aesar).