Acetic Anhydride → N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

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Reaction Steps

To a solution of 6-amino-3,4-dihydro-2H-naphthalen-1-one (CAS#3470-53-9, 0.875 g, 5.44 mmol) in pyridine (5 mL) is added acetic anhydride (0.83 g, 8.16 mmol). After 1 hour, the solution is diluted with dichloromethane and washed with water and 1M aqueous HCl. The organic phase is dried over sodium sulfate, filtered, and concentrated to give N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide; 1H NMR (400 MHz, CDCl3) δ ppm 2.09-2.16 (m, 2 H), 2.22 (s, 3 H), 2.59-2.67 (m, 2 H), 2.95 (t, J=6.1 Hz, 2 H), 7.21 (dd, J=8.3, 2.1 Hz, 1 H), 7.42 (br. s., 1 H), 7.70 (br. s., 1 H), 8.00 (d, J=8.3 Hz, 1 H).

Provenance & Evidence