N,N-Dimethylaniline → HCID 20463605, compound

Participants

Reaction Conditions

Reaction Steps

33g of 3-(m-diethylaminophenyl)-6-dimethylaminophthalide and 13g of dimethylaniline were dissolved in 300cc of tetrachloroethane. 14g of anhydrous aluminum chloride was added to the solution, and then the mixture was heated at 50° C for 3 hours with stirring. After the termination of reaction, 30% aqueous solution of caustic soda was added to the mixture to dissolve aluminum chloride while cooling with ice. Tetrachloroethane phase was steam distilled to remove unreacted dimethylaniline and tetrachloroethane. The remaining aqueous phase was neutralized with acetic acid to obtain a white solid. This solid was dissolved in 600cc of 2.5% aqueous solution of caustic soda, and then heated at 50° C. 600cc of 5% aqueous solution of potassium persulfate was added dropwise to the above solution, and then the mixture was heated at 60° C for 3 hours. After the termination of reaction, the resultant precipitates were filtered and recrystallized from methanol to obtain 31g of 3-(m-diethylaminophenyl)-3-(p-dimethylaminophenyl)-6-dimethylaminophthalide having the following structure whose m.p. was 177°-178° C in the form of colourless crystals. This compound become green on contact with silica gel. ##STR72##

Provenance & Evidence