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Synthese du dimethindene (indenyl‐ 14 C‐1)
Author(s) -
Mestre P.,
Noel J. P.,
Pichat L.,
Benakis A.
Publication year - 1982
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580190204
Subject(s) - chemistry , diethyl malonate , yield (engineering) , sodium hydroxide , hydrochloric acid , sodium carbonate , pyridine , barium carbonate , alkylation , malonate , carbanion , nuclear chemistry , medicinal chemistry , organic chemistry , sodium , catalysis , raw material , materials science , metallurgy
Synthesis of (1‐ 14 C‐indenyl) dimethindene (7‐ 14 C) benzyl chloride prepared from ( 14 C) barium carbonate is condensed with diethyl sodio malonate to give diethyl (7‐ 14 C) benzyl malonate : 4 in a yield of 78 %. 4 is then alkylated with 2‐dimethylamino 1‐chloroethane to give the diethyl dialkylmalonate : 12 . 12 is saponified with sodium hydroxide, decarboxylited by treatment with hot hydrochloric acid and cyclised with polyposphoric acid into 2‐(2‐dimethyl aminoethyl) 3‐(1‐ C) indanone : 8. This indanone is condensed with 2‐(2‐lithioethyl) pyridine, the intermediate is dehydrated into (1‐ C indenyl) Dimethindene which is isolated and purified as its maleate salt. Specific activity is 54 mCi/mMole. Radiochemical purity checked by TLC is better than 99%. The overall yield is 15.8 % based on barium carbonate.