Acetonitrile → HCID 70496719, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-amino-3-methyl-benzoic acid methyl ester (11.55 g, 70 mmol) and 3-bromobenzaldehyde (8.2 mL, 70 mmol) in acetonitrile (150 mL) were added isobutene (17 mL, 242 mmol) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (5.2 g, 8.4 mmol). The resulting mixture was stirred at 90° C. for 20 h in sealed tube. The mixture was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether) to afford 2-(3-bromo-phenyl)-4,4,8-trimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (8.15 g, 30%) as a light yellow solid: MS (ESI) M+1=388.0 & 390.0.

Provenance & Evidence