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In the single neck 250ml flask was added 5.6g 2-indanone and 40mL chloroform. 13mL 95% fuming nitric acid was measured. Both will be placed in a low temperature bath cooled to below -20C. Cooled 2-indanone was slowly added cooled fuming nitric acid. The reaction system was stirred vigorously while adding dropwise for 40 minutes. After the addition was complete by TLC trace (developing solvent: chloroform:methanol = 100:1, product Rf = 0.64,2- indanone Rf = 0.79). The reaction was continued at -20C for 20 minutes until reaction completion. With 60mL 10% sodium hydroxide solution was mixed with ice water to quench the reaction. The reaction system presents two layers in a separating funnel. The upper layer was extracted with chloroform (3 × 30mL). The combined organic phases was washed with saturated brine until neutral. The organic solvent was evaporated by a rotary evaporator to give a yellow solid. Recrystallization using ethyl acetate and cyclohexane then cooling gave reddish-brown crystals. Filtration gave 3.8g 5-nitro-2-indanone, yield 49.5%, mp 141-143C.
49.5%
With nitric acid; In chloroform; at -20℃;
It has been reported that 2-indanone is able to convert to 5-nitro-2-indanone by fuming nitric acid with vigorous stirring at -20 C according to modified published methodology [36] . To a cooled solution of 5.6 g 2-indanone in 40 mL chloroform was dropped slowly with 13 mL fuming nitric acid with vigorous stirring in 45 min at -20 C. After the addition was completed, the mixture was then stirred further for 20 min, poured into a mixture of sodium hydroxide (6.5 g) in water and ice (ca. 50 mL), and then extracted twice with ethyl acetate. The combined extracts were washed with water until neutral, dried over magnesium sulfate, and evaporated in vacuum to yield yellow solid. Chloroform was used as the eluent in column chromatography. Finally, the crude product was recrystallized from ethyl acetate/hexane to give 3.7 g of product (49.5% yield). m.p.:142-144 C (lit [36] 141-143 C).
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