Ammonia → HCID 18783990, compound

Participants

Reaction Steps

0.5 g (1.27 mmol) of 4-[4-(tert-Butoxycarbonylamino)butylamino]-2-chloro-3-nitroquinoline was dissolved in 13 ml of ethanol. 1.0 g (4.43 mmol) of tin chloride [II] dihydrate was added thereto and the mixture was refluxed under heating for one hour. The reaction mixture was poured into 2N aqueous ammonia. The resulting solution was extracted twice with chloroform, washed (brine), and dried (Na2SO4). The solvent was distilled off under reduce pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1 (v/v)) to collect the product. After the solvent was distilled off, the resulting product was triturated with diethyl ether to obtain 0.12 g (0.329 mmol) of 3-amino-4-[4-(tert-butoxycarbonylamino)butylamino]-2-chloroquinoline shown below as orange crystals. ##STR42## Its spectroscopic data are as follows: IR (KBr) cm- : 3270, 1680, 1540, 760. 1H-NMR (CDCl3) δ (ppm) : 1.44 (9H, s), 1.64 (4H, m), 3.17 (2H, q, J=6.0 Hz), 3.27 (2H, t, J=6.6 Hz), 3.89 (1H, H, br), 4.15 (2H, br), 4.59 (1H, br), 7.47 (2H, m), 7.77 (1H, d, J=7.6 Hz), 7.89 (1H, d, J=7.2 Hz).

Provenance & Evidence