Hydrochloric Acid → HCID 9859800, compound

Participants

Reaction Steps

To a solution of 5.0 g (0.020 mol) of 5,10-dihydro-8-methoxy-6-methylindeno[1,2-b]indole in 50 ml of tetrahydrofurane was added 8.1 g (0.080 mol) of morpholino borane and dropwise 6.3 ml of conc. hydrochloric acid. The initially exothermic reaction mixture was stirred at room temperature for 72 hour. An additional 6.3 ml of conc. hydrochloric acid was then added and the mixture stirred over night. 25 ml of water was then added and the mixture evaporated. The residue was suspended in 200 ml of water and 5 ml of conc. hydrochloric acid and the mixture was heated on a water bath until most of the solid material had dissolved. The solution was then filtered hot and the filtrate cooled and alkalinized by addition of 10M sodium hydroxide solution. Filtration and washing with water gave 1.93 g (38.4%) of the title compound 1H NMR (CDCl3) δ: 2.08 (3H,s), 3.15-3.25 (1H,dd), 3,42-3.55 (1H,dd), 3.7 (3H,s), 4.1-4.22 (1H,t), 5.22-5.28 (1H,d), 6.42-6.46 (1H,d), 6.6-6.65 (1H,d), 7.14-7,25 (3H,m), 7.3-7.4 (1H,m).

Provenance & Evidence