3-(4-Quinolyl)-2-propenylamine → 3-(Quinolin-4-yl)propan-1-amine

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Reaction Steps

Under a nitrogen atmosphere, 10% palladium on carbon (catalytic amount) was added to a solution of 3-(4-quinolyl)-2-propenylamine (Intermediate No. 2-4) (188 mg, 1.02 mmol) in methanol (3 ml) at room temperature, and the mixture was stirred under a hydrogen atmosphere overnight. The reaction mixture was filtered with Celite, the solvent was evaporated under reduced pressure, and the obtained residue was distributed between ethyl acetate (30 ml) and a saturated aqueous ammonium chloride solution (30 ml). A 4 N aqueous sodium hydroxide solution (30 ml) was added to the aqueous layer, the whole was extracted with chloroform (100 ml), and the obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the target compound (145 mg, 76.3%).

Provenance & Evidence