1-Indanone → 6-Nitroindan-1-one

Participants

Reaction Steps

To a solution of 1-indanone (30 g, 0.23 mol) in conc. H2SO4 (200 mL) was added a solution of KNO3 (34 g, 0.34 mol) in conc. H2SO4 (100 mL) at 0° C. The resulting mixture was stirred for 2 h, and then poured into ice-H2O (3 L). The mixture was extracted with EtOAc (3×500 mL). The combined organic layers were washed with brine (3×500 mL), dried (Na2SO4), filtered, concentrated and purified via column chromatography to afford 6-nitro-indan-1-one (25 g, 61% yield). 1H-NMR (300 MHz, DMSO-d6): □ 8.45 (d, J=8.4 Hz, 1H), 8.22 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 3.20 (t, J=6.0 Hz, 2H), 2.74 (t, J=6.0 Hz, 2H).

Provenance & Evidence