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

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).

1. additionAfter the resulting mixed solution
2. extractionwas extracted with ethyl acetate
3. washthe extract was washed with brine
4. dry with materialdried (Na2SO4)
5. distillationThe solvent was distilled off under reduced pressure
6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=300:1 (v/v))

ORD-Eintrag

ord-bc3dcd04d8c8482a85b7e7727cbd4f03

Quelldatensatz

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06069149