Hydrochloric Acid → HCID 15240193, compound

Participants

Reaction Conditions

Reaction Steps

To 150 ml of N,N-dimethylformamide, were added 10.0 g (30.7 mmol) of the above 5-(4-nitrobenzylidene)-5H-dibenzo[a,d]cycloheptene, 8.0 g (143 mmol) of reduced iron powder and 2.70 ml (30.6 mmol) of concentrated hydrochloric acid (d=1.18, 35%). The resulting mixture was heated to the inner temperature of about 70° C., and then heated and stirred for 3 hours at the same temperature. After the reaction was completed, the reaction mixture was cooled in an ice water bath, and about 12.4 ml of an aqueous 10% sodium hydroxide solution was added thereto, followed by stirring and thereafter suction filtration. The filtrate obtained was poured in about 1 liter of saturated brine, and extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. To thus obtained residue was added methanol, and the crystals precipitated were collected by filtration. The crystals were then recrystallized from methanol to give 8.41 g of 5-(4-aminobenzylidene)-5H-dibenzo[a,d]cycloheptene. Yield: 92.7%; m.p.: 119 to 120.0° C.

Provenance & Evidence