1,2,3,4-Tetrahydroisoquinoline → 3,4-Dihydroisoquinoline

Participants

Reaction Steps

18.8 ml of 1,2,3,4-tetrahydroisoquinoline(0.15M) was dissolved in 400 ml of dichloromethane; and 29.4 g of N-bromosuccinimide(0.165M) was slowly added thereto at room temperature followed by stirring for 30 minutes. To this, 100 ml of aqueous sodium hydroxide(30%) was added and further stirred for an hour. The organic layer was separated, washed with water and extracted from aqueous hydrochloric acid solution. Ammonia water was added to adjust the pH to 9; and extracted from dichloromethane, washed with water, dried over anhydrous sodium sulfate and concentrated to give 18.5 g of the title compound in oil form.

Provenance & Evidence