Acetic Anhydride → HCID 86756152, compound

Participants

Reaction Steps

Pyridine-3-carboxaldehyde (5.45 g, 0.051 mol) was dissolved in an excess of acetic acid anhydride (10 ml) and 4 drops conc. sulfuric acid added under stirring. The resulting red mixture was allowed to react at 70-75° C. for 7 days. The cooled, black coloured reaction mixture was diluted with CHCl3, washed twice with 10% aqueous NaHCO3 and then several times with brine. The organic phase was dried (MgSO4) and evaporated. The black crude product was dissolved in CHCl3, and impurities precipitated as pentane was added. Precipitates were removed. The solution was evaporated and the residual product distilled (Kugelrohr) under reduced pressure (140° C./0.2 mbar) to give a colourless oil. 1H- and 13C NMR (CDCL3), d (ppm) rel. to TMS: 8.80, 8.68, 7.83 and 7.37 (m, 4×1H, Ar-H), 7.73 (s, 1H, CH(OAc)2) and 2.14 (s, 6H, CH3); 168.443 (C=O), 150.778, 148.154, 134.303, 131.172 and 123.253 (Ar), 87.988 (CH(OAc)2) and 20.587 (CH3).

Provenance & Evidence