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Synthesis of 2, 7-bis [2-(diethylamino) ethoxy] fluoren-9 14C-one. 2HCL; (tilorone-914C hydrochloride

✍ Scribed by V. P. Gaur; A. Wacker

Publisher
John Wiley and Sons
Year
1973
Tongue
French
Weight
415 KB
Volume
9
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Tilorone hydrochloride bis‐deae‐fluorenone‐9^14^C) labelled with carbon‐14 in position 9 was synthesized in 8 steps on 0.5 millimolar scale. Starting from biphenyl‐2‐carboxylic‐^14^C‐acid (I), fluorenone‐9^14^C (II) and fluoren‐9^14^C (III) were prepared by established radiochemical procedures [1, 2, 3]. Sulfonation of III gave fluoren‐9^14^C‐2, 7‐disulfonic acid (IV), which was converted to its potassium salt and oxidized with KMnO~4~ to obtain 9‐oxo‐9^14^C‐disulfonic acid dipotassium salt (V) in yields of 60% and 80% respectively. This was fused with NaOH at 325°C to get 4,4′‐dihydroxybiphenyl‐2‐carboxylic‐^14^C‐acid (IV) in 67% yield. VI on dehydration with ZnCl~2~ gave 2, 7‐dihydroxy‐9‐oxo‐fluoren‐9^14^C (VII) with 82% yield.

Condensation of VII with 2‐diethylaminoethyl chloride in presence of KOH resulted in the synthesis of the title compound in overall yield of 15% based on the amount of I used.

Characterisation data to establish the chemical and radiochemical purity are included. The labelled preparation showed the same biological activity [16] as an authentic specimen [23] of the inactive compound.

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