N-(2-Methylbut-3-yn-2-yl)aniline → 2,2-Dimethyl-1,2-dihydroquinoline

Participants

Reaction Steps

A mixture of N-[3,3-dimethylpropyn-3-yl]aniline and cuprous chloride (3.9 g) in toluene (140 mL) was refluxed under nitrogen for 4½ hrs. The reaction mixture was filtered and the filtrate washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane:hexane (1:1) to provide the desired compound.

Provenance & Evidence