Sodium Cyanide → 6-Methoxy-9-oxo-9H-xanthene-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of finely ground sodium cyanide (1.3 g, 26.5 mmol) and 3-fluoro-6-methoxy-xanthen-9-one (2.3 g, 9.42 mmol) in N,N-dimethylformamide (30 mL) was heated at 100° C. for 4 hours. Sodium cyanide (0.7 g, 14.3 mmol) was added and heating continued an additional hour. The mixture was allowed to cool to room temperature, then poured into ice water (˜150 mL). The product was collected by filtration, washed with water and air dried to give Compound 5i, 1.42 g (60%). MS: m/z 251.9 (MH+). 1H NMR (CDCl3): δ 3.96 (s, 3H), 6.91 (d, 1H, J=2.3 Hz), 7.00 (d of d, 1H, J=2.3 & 8.9 Hz), 7.61 (d of d, 1H, J=1 & 8.1 Hz), 7.79 (d, 1H, J=1 Hz), 8.24 (d, 1H, J=8.9 Hz) and 8.42 (d, 1H, J=8.1 Hz).

Provenance & Evidence