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To a solution of 5.59 g (31.9 mmol) of 5-acetamidoindan in 55 mL of H2SO4 kept in an ice-bath was added portionwise 3.62 g of KNO3 (35.8 mmol). The solution was stirred in the ice-bath for 2 h and at room temperature overnight. It was added to 500 mL of ice-water and stirred for 1 h. The precipitate was filtered, washed with water, and dried to leave a black solid, which was separated by chromatography (silica gel, eluted with hexane/ethyl acetate=10:1) to give 1.06 g (15%) of a yellow solid. 1H NMR (CDCl3), 2.142 (m, 2), 2.279 (s, 3), 3.00 (m, 4), 8.44 (s, 1), 8.575 (s, 1), 10.389 (s, 1).

1. filtrationThe precipitate was filtered
2. washwashed with water
3. customdried
4. customto leave a black solid, which
5. customwas separated by chromatography (silica gel, eluted with hexane/ethyl acetate=10:1)