Sodium hydride → 2-(2-oxopyrrolidin-1-yl)-N-(3-methyl-5,6,7,8-tetrahydrothieno[2,3-b]quinolin-4-yl)acetamide

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Reaction Steps

Into a suspension of 1.26 g of sodium hydride (60% content) in 15 ml of N-ethylpyrrolidone, was added 3.28 g of 4-amino-3-methyl-5,6,7,8-tetrahydrothieno[2,3-b]quinoline at room temperature. The mixture was heated to 50.degree. C. and stirred for 40 minutes. Thereafter, 4.72 g of methyl 2-oxo-1-pyrrolidine acetate was added dropwise to the mixture at 50.degree. C. over a period of 30 minutes. After the stirring at 50.degree. C. for 20 minutes, the mixture was cooled to 15.degree. C. and poured into 130 ml aqueous solution containing 13.5 g of ammonium chloride. After extraction of the solution with 100 ml of chloroform, the extract was dried over anhydrous sodium sulfate, followed by evaporation to dryness. The resultant product was added with ethyl acetate, pulverized and filtered. The crude crystals were recrystallized from chloroform-ethyl acetate to obtain 4.31 g of the titled compound having the melting point of 244.degree. to 246.degree. C.

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