4-(2-((4-Nitronaphthalen-1-yl)oxy)ethyl)morpholine → 4-(2-Morpholinoethoxy)naphthalen-1-amine

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Reaction Steps

A mixture of 4-[2-(4-nitro-naphthalen-1-yloxy)-ethyl]-morpholine (10 g, 33.0 mmol), MeOH (80 ml) and Pd/C (10%, 1.0 g) is shaken under a hydrogen atmosphere at 30 psi for 4 hours. The mixture is then filtered through a bed of Celite under a stream of nitrogen. The filtrate is reduced under vacuum to give 4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-ylamine (7.32 g, 81.3%). 1H NMR (300 MHz, CDCl3) δ8.21 (m, 1H), 7.81 (m, 1H), 7.49 (m, 2H), 6.69 (s, 2H), 4.23 (t, 2H), 3.76 (t, 4H), 2.92 (t, 2H), 2.65 (t, 4H). MS: 273 (M+1).

Provenance & Evidence