[CH3:1][N:2]([CH3:18])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[CH2:15][CH3:16])=[CH:9][CH:8]=1)=[O:6].[H-].[Na+].[H][H].[CH3:23]I>CN(C)C=O>[CH3:18][N:2]([CH3:1])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([N:13]([CH3:23])[C:14](=[O:17])[CH2:15][CH3:16])=[CH:11][CH:12]=1)=[O:6]
A soluton of 3.10 g of N-[4-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]propanamide in 25 ml dimethylformamide was stirred in an inert atmosphere and 0.60 g of sodium hydride (60% oil suspension) was added. After stirring for 1 hour, the liberation of hydrogen had ceased and a solution of 1.8 g of methyl iodide in 5 ml of dimethylformamide was added portionwise. After stirring for an additional hour, the system was evaporated to remove volatiles and then the reaction mixture was triturated 3 times with hexane (3×50 ml). The reaction mixture was carefully poured into cold water and extracted with methylene chloride. The methylene chloride solution was dried and evaporated to dryness at reduced pressure to yield a crystalline solid. Recrystallization from methylene chloridehexane gave a yellow crystalline solid, mp 76°-78° C.
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