Methyl iodide → HCID 20362684, compound

Participants

Reaction Conditions

Reaction Steps

0.023 moles of sodium hydride is added slowly, while stirring, to a solution of 2.0 g. (0.011 moles) of 8-methyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one in 60 ml. of dimethylformamide, followed by heating at 80° C. for 80 minutes. The reaction mixture is cooled in an ice bath and 6.5 g. (0.046 moles) of methyl iodide added dropwise, the rate of addition being regulated so as to maintain the temperature of the reaction mixture at about 10° C. When the addition is complete, the temperature is raised slowly to 60° C. and then maintained at this level for 3 hours. The reaction mixture is evaporated to dryness in vacuo and the solid residue is extracted with chloroform. The organic solution is washed twice with water, dried over anhydrous sodium sulfate, filtered and then evaporated to dried over anhydrous sodium sulfate, filtered and then evaporated to dryness in vacuo. The solid residue is taken up in diisopropyl ether, filtered over active carbon and recrystallized from diisopropyl ether. 2,8-Dimethyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one is obtained in a yield of 55% of theory. M.P. 75°-76° C.

Provenance & Evidence