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Publication No: WO2023067624 [World Intellectual Property Organization (WIPO)] Application No: WO2022IN50931A
Title: A PROCESS FOR THE PREPARATION OF 2,7-DIHYDROXY-9-FLUORENONE USEFUL FOR THE SYNTHESIS OF TILORONE AND ITS SALTS
Publication Date: 27-04-2023 File Date: 19-10-2022
Inventor(s): Jaisankar, Parasuraman; Deb, Indubhusan; Bhattacharjee, Pinaki
IPC Classification: A61K 0031343, C07C 021302, C07C 021722
Abstract:
The present invention provides a method for the preparation of building blocks of 2,7-dihydroxy-9-fluorenone towards the synthesis of tilorone dihydrochloride salt and other salts (bromide, iodide, fluoride, citrate, oxalate, maleate, phosphate, tartrate, triflate, trifluoroacetate, tetrafluoroborate) of Tilorone. An efficient, safe, cost effective method for the preparation of 2,7-bis-[2-(diethylamino)ethoxy]-fluorenone-9 and its various salts is developed. Method involves oxygenation of fluorene, nitration of fluorenone followed by reduction and diazotization towards the formation of 2,7-dihydroxy-9-fluorenone which is the key intermediate for the formation of 2,7-bis-[2-(diethylamino)ethoxy]- 9- fluorenone- dihydrochloride (Tilorone dihydrochloride) and other tilorone salts. The current synthesis method of the invention has relatively simple operation, mild reaction conditions, high yield and simple process with, yield 80-97%. Subsequent product purification of this method uses filtration and crystallization methods, avoiding the existing methods of column chromatography.

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Industrial Applications Chemistry, Chemical Processes Polymers [Chemistry, Chemical Processes]