N,N-Dimethylaniline → HCID 22414869, compound

Participants

Reaction Conditions

Reaction Steps

5.67 g (24.5 mmol) of 4-allyloxy-2,3-dihydro-3,3,7-trimethyl-1H-indol-2-one was added to 13 ml of N,N-dimethylaniline and the mixture was heated with stirring for 17 hours at 205° C. under a nitrogen atmosphere. After the reaction, N,N-dimethylaniline was removed by evaporation under reduced pressure. The residue was dissolved in chloroform and washed with water, 2N hydrochloric acid, and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was purified by column chromatography (silica gel, 10:1 mixture of chloroform and ethyl acetate) and precipitated in n-hexane. Filtration of the precipitate afforded 4.77 g (yield, 84.1%) of light yellow crystals of the title compound.

Provenance & Evidence