HCID 18783946, compound → tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamate

Participants

Reaction Steps

38.69 mg (97.98 mmol) of 4-[4-(tert-butoxycarbonylamino)butylamino]-2-chloro-3-nitroquinoline was dissolved in 900 ml of methanol. 10 g of 10% palladium-carbon was added thereto and the mixture was stirred for 2 days under hydrogen atmosphere. The reaction mixture was filtrated and the filtrate was concentrated under reduced pressure. A sodium hydrogencarbonate aqueous solution was added to the residue and the solution was extracted twice with chloroform. The organic phase was washed with brine and dried (Na2SO4). The solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 10:1 (v/v)) to obtain 21.37 mg (64.67 mmol) of 3-amino-4-[4-(tert-butoxycarbonylamino)butylamino] quinoline shown below as a green brown amorphous substance. ##STR50## Its spectroscopic data are as follows: 1H-NMR (CDCl3) δ (ppm): 1.44 (9H, s), 1.64 (4H, m), 3.16 (2H, m), 3.26 (2H, t, J=6.8 Hz), 3.8 (2H, br) 4.6 (1H, br), 7.45 (2H, m), 7.82 (1H, m), 7.97 (1H, m), 8.47 (1H, s).

Provenance & Evidence