Water → Methyl 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydroimidazo[4,5-a]quinolizine-10-carboxylate

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Reaction Steps

3.50 g (21.2 mmol) of 1-methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thione were dissolved in 0.6 1 of 1,3-dimethyl-2-imidazolidinone at 140° C., left to cool to room temperature, treated with 5.9 g (21.4 mmol) of 3-(3-benzyloxyphenyl)-oxirane-2,2-dicarbonitrile and stirred over the weekend. Then, 7.8 ml of methyl propiolate were added and the mixture was stirred at 110° C. for 22 hours. After cooling the solution was stirred into 6 l of water, the precipitate was filtered off and it was chromatographed over silica gel with dichloromethane/acetone/hexane 2:1:1. There were obtained 3.20 g (34%) of methyl 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo[4,5-a]quinolizine-10-carboxylate as yellow crystals with m.p 196-198° C.

Provenance & Evidence