Hydrochloric Acid → HCID 57308572, compound

Participants

Reaction Steps

16 ml dioxane, 1.3 g (4.9 mmol) 5,10-dihydro-4,6-dimethyl-8-methoxyindeno[1,2-b]indole and 1.98 g (19.6 mmol) morpholineborane were added to a round bottom flask. 4 ml hydrochloric acid (conc.) was added dropwise during stirring of the solution. The reaction mixture was refluxed for 1 hour. 8 ml (6M) hydrochloric acid was added and the solution was refluxed for 30 min. After the solution had reached room temperature, 50 ml water was added. The mixture was made basic with NaOH(aq) until pH 9. The product was extracted with dichloromethane two times. The organic phase was dried with Na2SO4 and the solvent was evaporated. The product was subjected to chromatography in dichloromethane. The isolated product was dissolved in acetonitrile, a saturated solution of HCl(g) in ether was added and the product precipitated as the hydrochloride salt and was removed by filtration. 1.2 g (82.2%) of product was isolated. 1H NMR (CDCl3):2.33 (3H,s), 2.48 (3H, s), 2.95 (1H, dd), 3.56 (1H, dd), 3.77 (3H, s), 4.44 (1H, ddd), 5.71 (1H, d), 6.78 (1H, s), 6.93 (1H, s), 7.11-7.17 (2H, m), 7.30 (1H, d).

Provenance & Evidence