Aniline → HCID 302917, compound

Participants

Reaction Steps

4,5-Dichloro-2-nitroaniline (9.8 g, 47.4 mmol), 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (18.5 g, 57.4 mmol, Allied Signal, Buffalo), and acetonitrile (300 mL) were combined and the mixture was heated to reflux for several hours. After thin-layer chromatography showed that no starting aniline remained, the mixture was allowed to cool to rt and was poured into ethyl acetate, causing a precipitate to form. The mixture was filtered through a pad of Celite, purified by silica gel and the solvents were removed in vacuo to provide a brown solid (3.9 g, 37%); 1H NMR (DMSO-d6) δ: 8.11 (d, J=2.2 Hz, 1H, Ar—H), 7.67 (br s, 2H, NH2).

Provenance & Evidence