Hydrochloric Acid → HCID 15240193, compound

Participants

Reaction Conditions

Reaction Steps

10.0 g (30.7 m moles) of 5-(4-nitrobenzylidene)-5H-dibenzo[a,d]cycloheptene, 8.0 g (143 m moles) of reductive iron powder, and 2.70 ml (30.6 m moles) of concentrated hydrochloric acid (d: 1.18, 35%) were added to 150 ml of N,N-dimethyl formamide, and the mixture was heated at an inside temperature of about 70° C., and stirred at that temperature with heating for 3 hours. After the end of reaction, the mixture was cooled over an ice-water bath, admixed with about 12.4 ml of an aqueous 10% NaOH solution, stirred and subjected to filtration by suction. The filtrate was poured into about 1l of an aqueous saturated NaCl solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was removed therefrom under reduced pressure. The residue was admixed with methanol, and the precipitated crystal was recovered therefrom by filtration. The thus obtained crystal was recrystallized from methanol, whereby 8.41 g of 5-(4-aminobenzylidene)-5H-dibenzo[ a,d]cycloheptene was obtained (yield: 92.7%). The melting point was 119°-120.0° C. Elemental analysis as C22H17N was as follows:

Provenance & Evidence