Methyl iodide → HCID 68829536, compound

Participants

Reaction Steps

To a solution of tert-butyl N-[3-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]glycinate (3.0 g, 7.0 mmol) in tetrahydrofuran (10 ml) was added trifluoroacetic acid (820 ml), and the mixture was stirred at room temperature for 6 hrs. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl-acetate and water. The aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue (3.0 g) was dissolved in N,N-dimethylformamide (10 ml). Thereto were added methyl iodide (1.5 g, 5.3 mmol) and potassium carbonate (0.73 g, 5.3 mmol) and the mixture was stirred at room temperature for 2 days. The reaction mixture was partitioned between ethyl acetate and water, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, washed successively with 0.1 M aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give methyl N-[3-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]glycinate (1.6 g, yield 79%) as a pale-yellow powder. Subsequently, methyl N-[3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]glycinate (1.0 g, yield 62%, pale-yellow powder) was synthesized by a method similar to the method shown in Example 25(2).

Provenance & Evidence