HCID 22285715, compound → HCID 178526399, compound

Participants

Reaction Steps

To a solution of 3-nitro-5,6,7,8-tetrahydro-naphthalen-1-ylamine (5.9 g, 31.0 mmol) prepared in Step A in glacial acetic acid (100 mL) was added a solution of sodium nitrite (2.13 g, 31.0 mmol) in water (5.0 mL) at 0° C., and the resultant dark solution was stirred at this temperature for 20 h. The volatiles were evaporated and the residue was basified with a saturated solution of sodium bicarbonate (100 mL). The aqueous was extracted with ethyl acetate (4×200 mL) and the combined extracts were washed with brine, dried (MgSO4) and evaporated to a residue that was purified by column chromatography (silica, 20% to 30% gradient of ethyl acetate in hexane) to give an oil (3.8 g, 60%): MS (ES) m/z 204 (M+); 1H NMR (CDCl3) δ 8.22 (1H,s), 7.77 (1H, s), 3.06 (4H, m), 2.26 (2H, m).

Provenance & Evidence