HCID 11164425, compound → 2-[4-Benzyloxy-2-aminonaphthalen-1-yl]ethyl acetate

Participants

Reaction Steps

A solution of 2-[4-benzyloxy-2-nitronaphthalen-1-yl]ethyl acetate (0.2 g, 0.55 mmol) in THF (30 mL) was added to a suspension of PtO2 (100 mg) in THF (10 mL) and the suspension was hydrogenated (with shaking) at 55 psi at room temperature for 1 h. The suspension was filtered over Celite and the filtrate was concentrated in reduced pressure to yield 2-[4-benzyloxy-2-aminonaphthalen-1-yl]ethyl acetate as a brown solid (0.18 g, 97.58%). Mp 76-82° C; 1H NMR (CDCl3, 500 MHz) δ 8.24 (d, 8.0, 1H), 7.80 (d, 8.5, 1H), 7.22-7.53 (m, 7H), 6.41 (s, 1H), 5.20 (s, 2H), 4.25 (t, 8.0, 2H), 3.21 (t, 8.0, 2H),2.11 (s, 3H); EIMS m/z 335 (M+); IR (neat) νmax 3378, 2927, 1731, 1624, 1600, 1516, 1454, 1410, 1366, 1239, 1158, 1133, 1028, 827, 759, 698 cm−1.

Provenance & Evidence