4-Chloroaniline → HCID 67290739, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 4-chloro-phenylamine (10.2 g, 80 mmol), 2-nitrobenzaldehyde (12.1 g, 80 mmol), and 2-methylpropene (25 ml, pre-cooled to −78° C.) in acetonitrile was added ytterbium trifluoromethanesulfonate (1.3 g, 2.1 mmol) at ice-bath. The resulting mixture was stirred at 80° C. for 16 h in sealed tube. The reaction mixture was cooled to 0° C. The mixture was concentrated in vacuum. The residue was diluted with water, extracted with diethyl ether. The extracts were washed with brine and then dried over anhydrous sodium sulfate, concentrated in vacuo. The residue was purified by column chromatography to give 6-chloro-4,4-dimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (7.8 g, 30.8%). LC/MS m/e obsd. (ESI+) [(M+H)+] 317.1.

Provenance & Evidence