Methyl iodide → HCID 67289277, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-(3-bromo-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (4.2 g, 12.4 mmol) in N,N-dimethylformamide (15 mL) was added a 60% dispersion of sodium hydride in mineral oil (1.5 g, 37.2 mmol) portionwise at 0° C. The mixture was stirred at 0° C. for 30 min and then iodomethane (2.4 mL, 37.2 mmol) was added to above mixture dropwise at 0° C. The solution was stirred at 0° C. for 2 h and then extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The yellowish residue was purified by ISCO combi-flash chromatography (gradient elution, 10% ethyl acetate/hexane) to afford 2-(3-bromo-phenyl)-1,4,4-trimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (1.1 g, 70%) as a yellow oil: MS obsd. (ESI+) [(M+H)+] 355.0 & 357.0.

Provenance & Evidence