Water → 2-Benzoyl-1-(3,4,5-trimethoxybenzyl)-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline

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Reaction Steps

To a stirred solution of 1.7 g (5.17 mmole) of 2-benzoyl-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline, 1.16 g (5.37 mmole) of 3,4,5-trimethoxybenzyl chloride and 0.118 g (0.517 mmole) of benzyltriethylammonium chloride in 25 ml of toluene, under nitrogen, was added 7.2 ml of 50% sodium hydroxide solution. The mixture was stirred vigorously at ambient temperature for 2 hours, and then 25 ml of water and 25 ml of methylene chloride was added. The organic layer was separated, washed with water, dried over magnesium sulphate and concentrated to give 2-benzoyl-1-(3,4,5-trimethoxybenzyl)-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline, m.p. 193°-195° C., after recrystallization from acetonitrile.

Provenance & Evidence