Hydrochloric Acid → 1-Nitrosoindoline

Participants

Reaction Steps

To a solution of 2,3-dihydro-1H-indole (10.0 g, 84 mmol) in acetic acid (100 ml) at 0° C. was added dropwise a solution of sodium nitrite (6.08 g, 88 mmol) in water (25 ml) so that the temperature was maintained below 5° C. After 1 hour water (500 ml) and 1 M hydrochloric acid (500 ml) were added to the precipitate that formed. The mixture was stirred for another hour before the product was filtered off, washed with water (3×100 ml) and dried under vacuum to give 1-nitroso-2,3-dihydro-1H-indole as a brown solid (5.27 g). 400 MHz 1H NMR (DMSO-d6) δ: 7.8 (d, J=7.6 Hz 1H), 7.45 (d, J=7.6 Hz, 1H), 7.37 (t, J=7.6 Hz 1H), 7.29 (t, J=7.6 Hz, 1H), 4.09 (m, 2H), 3.19 (t, J=7.6 Hz, 2H); LCMS: 149 [M+H]

Provenance & Evidence