Aluminum(III) Chloride → 3-(2-Amino-6-phenoxy-3,4-dihydro-quinolin-3-yl)-N-cyclohexyl-N-methyl-propionamide

Participants

Reaction Steps

5-(2-amino-5-phenoxy-phenyl)-4-cyano-pentanoic acid cyclohexyl-methyl-amide (0.20 g, 0.46 mmol) was dissolved in toluene (5 mL), followed by addition of aluminum chloride (0.184 g, 1.38 mmol). The reaction mixture was heated to reflux for 10 minutes and was then allowed to cool to room temperature. The crude reaction mixture was poured into a separatory funnel and partitioned between ethyl acetate and 10% aqueous Na2CO3 solution. The organic layer was washed 2 more times with 10% aqueous Na2CO3 solution and one time with saturated brine solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield a residue which was purified by flash chromatography using chloroform:methanol:triethylamine as the mobile phase to yield the title compound as a residue.

Provenance & Evidence