1-Chloro-3-iodopropane → 3-(3-chloropropyl)-1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one

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Reaction Steps

A solution of 1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (350 mg, 1.12 mmol) in 10 mL THF was cooled to −78° C. (acetone/dry ice bath) then treated with lithium hexamethyldisilazine (1.23 mL of a 1M solution in THF). The resulting dark solution was stirred for 30 minutes then treated with 1-iodo-3-chloropropane dropwise. The mixture was allowed to warm to room temperature and kept at this temperature overnight. The reaction was quenched with brine and extracted with 3×50 mL CH2Cl2. The combined organic fractions were dried over MgSO4, filtered and concentrated to give a dark residue which was subjected to flash chromatography on silica gel using CH2Cl2. A yellow viscous oil was obtained (130 mg, 29.8%). 1H-NMR (CDCl3) δ: 8.08-8.00 (m, 2H), 7.12-7.09 (m, 2H), 7.00 (d, J=8.7 Hz, 1H), 6.86-6.84 (m, 2H), 5.15 (dd, J=4.2, 20.4 Hz, 2H), 3.76 (s, 3H), 3.60 (t, J=6.3 Hz, 2H), 3.17 (dd, J=5.4, 15.6 Hz, 1H), 2.93-2.71 (m, 2H), 2.05-1.67 (m, 4H).

Provenance & Evidence