Hydrochloric Acid → HCID 66737937, compound

Participants

Reaction Conditions

Reaction Steps

5 g (42 mmol) of indoline are dissolved in 50 ml of toluene. In a separate flask, 70 ml of toluene are cooled to 5° C., and 100 ml of boron trichloride (10% solution in xylene) are added dropwise at this temperature under nitrogen. The indoline is subsequently added dropwise to this solution at 5-10° C., and 5.4 g (46 mmol) of 4-aminobenzonitrile are subsequently added in portions over the course of 30 min. The mixture is stirred at 5-10° for a further 15 min, and 6.7 g (50 mmol) of aluminium chloride are then added in portions at the temperature indicated. The mixture is heated under reflux for 6 h. For work-up, the reaction mixture is cooled to 70° C., and 10 ml of water are added dropwise, during which the temperature rises slightly and the solution becomes cloudy. 60 ml of 2 N hydrochloric acid are subsequently added, during which a clear solution is again formed, and the mixture is warmed under reflux for 12 h. The reaction mixture is poured into ice-water, adjusted to pH=12 using conc. NaOH and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated, and the residue is chromatographed over a column with ethyl acetate. The combined product fractions are recrystallised from petroleum ether, giving 3.8 g of yellow crystals (4-aminophenyl)-(2,3-dihydro-1H-indol-7-yl)methanone. (M.p. 133-135° C.)

Provenance & Evidence