Iodoethane → HCID 24771191, compound

Participants

Reaction Steps

A solution of 3,3,6-trimethyl-2,3,4,7-tetrahydroindolo[2,3-c]quinolin-1-one of Example 4 (0.28 g, 1 mmol) in anhydrous N,N-dimethylformamide (4 mL) was added dropwise at room temperature under stirring to a suspension of sodium hydride (60% dispersion in mineral oil, 0.051 g, 1.3 mmol) in anhydrous N,N-dimethylformamide (4 mL). The reaction mixture was stirred for 2 h at room temperature, and then 1-iodoethane (0.19 g, 1.2 mmol) was added dropwise. The mixture was stirred at room temperature until the reaction was completed (4 h, thin layer chromatography control). The reaction mixture was diluted with water (25 mL) and brine (10 mL), and then extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over anhydrous sodium sulfate, and ethyl acetate was distilled off in vacuum to give the crude product (0.18 g, 60%). Crystallization from hexanes yielded the pure product as light orange crystals; m.p. 174-177° C.

Provenance & Evidence