tert-Butyl (3-aminopropyl)carbamate → 4-[3-(Tert-butoxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline

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Reaction Steps

0.59 g (2.41 mmol) of 2,4-Dichloro-3-nitroquinoline and 0.42 g (2.41 mmol) of N-(tert-butoxycarbonyl)-1,3-propanediamine were heated at 70° C. in 10 ml of triethylamine and stirred for 1.5 hours. Triethylamine was distilled off under reduced pressure. The resulting residue was dissolved in methylene chloride, washed with water, and dried (Na2SO4). After the solvent was distilled off under reduced pressure, the residue was triturated with methanol and filtered to obtain 0.61 g (1.60 mmol) of 4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline shown below as yellow crystals (mp: 159-161° C.). ##STR34## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3310, 1680, 1580. 1H-NMR (CDCl3) δ (ppm) : 1.50 (9H, s), 1.77 (2H, m), 3.27 (2H, q, J=6.1 Hz), 3.36 (2H, q, J=6.0 Hz), 4.82 (1 H, br), 7.37 (1H, br), 7.55 (1H, t, J=7.8 Hz), 7.72 (1H, t, J=7.7 Hz), 7.89 (1H, d, J=8.2 Hz), 8.27 (1H, d, J=8.4 Hz).

Provenance & Evidence