Ammonia → 7-Ethoxy-5,8-dihydronaphthalen-1-amine

Participants

Reaction Conditions

Reaction Steps

The product of Example 1D (1.8 g, 9.63 mmol) and tert-butanol (2.13 g, 28.8 mmol) were dissolved in tetrahydrofuran (20 mL) in a 3-neck 1000 mL round-bottom flask, and the solution was cooled to −78° C. Ammonia (˜35 mL) was condensed into the flask, then lithium metal was added (wire, 225 mg, 32.4 mmol) in portions over 10 min. The reaction mixture was stirred at −78° C. for 1 h, quenched with methanol (50 mL) and H2O (50 mL). The reaction was allowed to stir overnight at room temperature to allow NH3 to evaporate, then it was diluted with ethyl acetate (300 mL), washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel, eluting with 15%-25% ethyl acetate-hexanes, to afford the title compound as a brown oil (999 mg, 55%). 1H NMR (DMSO-d6) δ 6.82 (t, 1H, J=7.6 Hz), 6.44 (d, 1H, J=7.1 Hz), 6.35 (d, 1H, J=7.5 Hz), 4.80 (s, 2H), 4.78 (t, 1H, J=3.8 Hz), 3.78 (q, 2H, J=7.1 Hz), 3.36 (q, 2H, 4.8 Hz), 3.00 (t, 2H, J=4.9 Hz), 1.26 (t, 3H, J=7.1 Hz); MS (DCI+) m/z 190 (M+H).

Provenance & Evidence