116530-60-0

Add 5.6 g of 2-indanone and 40 mL of chloroform to a 250 mL single neck flask. Measure 13 mL of 95% fuming nitric acid. Both were cooled in a cryogenic bath at a temperature below -20°C. The cooled 2-indanone was slowly added to the cooled fuming nitric acid. The dropwise addition process was continued for 40 minutes under vigorous stirring. The progress of the reaction was monitored by thin layer chromatography (TLC) (unfolding agent: chloroform:methanol=100:1, product Rf=0.64, 2-indanone Rf=0.79). After dropwise addition was complete, the reaction was continued at -20°C for 20 min to ensure complete reaction. The reaction was quenched with 60 mL of 10% sodium hydroxide solution mixed with ice water. The reaction mixture was layered in a dispensing funnel. The upper aqueous phase was extracted with chloroform (3 x 30 mL). The organic phases were combined and washed with saturated saline until neutral. The organic solvent was evaporated using a rotary evaporator to give a yellow solid. Recrystallized by ethyl acetate and cyclohexane and cooled to give reddish brown crystals. Upon filtration, 3.8 g of 5-nitro-2-indanone was obtained in 49.5% yield with a melting point of 141-143°C. The crystals were purified by filtration.

[1] Journal of the American Chemical Society, 1997, vol. 119, # 52, p. 12722 - 12726
[2] Patent: CN105315204, 2016, A. Location in patent: Paragraph 0028; 0032; 0033
[3] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 738 - 747
[4] Chemische Berichte, 1899, vol. 32, p. 28,31