Water → HCID 66725171, compound

Participants

Reaction Steps

A solution of (4R)-4-(3-amino-4-chloro-6-nitrophenyl)pyrrolidin-2-one (3.5 g, 13.7 mmol) in 12.6 mL of conc. H2SO4 was heated to 55° C. Sodium nitrite (16.94 mmol) was added in small portions. The reaction mixture turned from yellow to red, then dark red. After the mixture was stirred for additional 30 min at this temperature, the mixture was cooled to room temperature and water was added. The mixture was then extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with water and brine, and dried over Na2SO4. The solvent was removed in vacuo to afford the title compound (2.5 g, 80% yield). 1H-NMR (400 MHz, CD3OD): δ 2.45-2.51 (dd, J=17.2, 6.8 Hz, 1H), 2.77-2.84 (dd, J=17.2, 9.2 Hz, 1H), 3.41-3.44 (m, 1H), 3.80-3.85 (dd, J=10.4, 8.0 Hz, 1H), 4.03-4.05 (m, 1H), 7.61-7.63 (d, J=8.4 Hz, 1H), 7.67-7.70 (dd, J=8.4, 2.0 Hz, 1H), 7.91 (d, J=2.0 Hz, 1H); MS (ESI) m/z 241.01 (M+H)+.

Provenance & Evidence