Hydrochloric Acid → 3-Amino-4-[3-(benzyloxycarbonylamino)propylamino]-2-chloroquinoline

Participants

Reaction Steps

0.27 g (0.651 mmol) of 4-[3-(benzyloxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline was dissolved in 10 ml of methanol. One ml of concentrated hydrochloric acid and 0.22 g (0.390 mmol) of iron powder were added thereto and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into a saturated sodium hydrogencarbonate aqueous solution. After the resulting mixed solution was extracted with ethyl acetate, the extract was washed with brine and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=300:1 (v/v)) to obtain 0.12 g (0.312 mmol) of 3-amino-4-[3-(benzyloxycarbonylamino)propylamino]-2-chloroquinoline shown below as faint yellow powder. ##STR30## Its spectroscopic data are as follows: 1H-NMR (CDCl3) δ (ppm) :1.76 (2H, m), 3.30 (2H, m), 3.42 (2H, q, J=6.3 Hz), 4.21 (2H, b r), 4.44 (1H, br), 4.92 (1H, br), 5.16 (2H, s), 7.30~7.39 (5H, m), 7.46 (2H, m), 7.89 (2H, m).

Provenance & Evidence