Ammonia → 3-Amino-4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-quinoline

Participants

Reaction Steps

0.27 g (0.70 mmol) of 4-[3-(tert-Butoxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline was dissolved in 7 ml of ethanol. Tin chloride [II] dihydrate (0.55 g, 2.45 mmol) was added thereto and the mixture was refluxed under heating for 1 hour. After cooling, the reaction mixture was poured into 2N aqueous ammonia. The resulting solution was extracted twice with chloroform, thereafter the extract was washed (brine), and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1 (v/v)) to obtain 0.15 g (0.428 mmol) of 3-amino-4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-quinoline shown below as pale yellow crystals. ##STR35## Its spectroscopic data are as follows: 1H-NMR (CDCl3) δ (ppm) : 1.49 (9H, s), 1.73 (2H, m), 3.29 (2H, t, J=6.2 Hz), 3.35 (2H, q, J=6.0 Hz), 4.28 (2H, br), 4.60 (1H, br), 4.75 (1H, br), 7.44 (2H, m), 7.87 (1H, d, J=7.6 Hz), 7.94 (1H, d, J=7.6 Hz).

Provenance & Evidence