HCID 53392262, compound → HCID 28419113, compound

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Reaction Steps

A suspension of N,N-diethyl-2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine (0.85 g, 3.06 mmol) and palladium on charcoal, 10% wt (0.163 g, 0.153 mmol) in ethanol (30 mL) was stirred at room temperature under a balloon of hydrogen overnight. The mixture was filtered through a pad of celite. The celite pad was rinsed with 20 mL of methanol. The filtrate was concentrated and the residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in methanol/95% CH2Cl2 to give a dark brown residue (685 mg, 90%). 1H-NMR (CDCl3) δ 6.63-6.32 (m, 3H), 3.37-3.23 (m, 4H), 2.74-2.56 (m, 8H), 1.93 (t, J=5.7 Hz, 2H), 1.08 (t, J=7.2 Hz, 6H). MS (ESI): 248.2 (M+1).

Provenance & Evidence