Hydrochloric Acid → 5-Nitro-2-(pyridin-2-ylmethoxy)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

2-hydroxy-5-nitrobenzaldehyde (5.0 g, 29.9 mmol), potassium carbonate (4.12 g, 29.9 mmol) and caesium carbonate (9.74 g, 29.9 mmol) were mixed in DMF (30 ml). Picolyl chloride.HCl (5.39 g, 32.9 mmol) was added and the mixture then heated at 100° C. for 5 hours. The reaction mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate, dried and evaporated. Trituration of the residue in ether provided 5-nitro-2-(pyridin-2-ylmethoxy)benzaldehyde as a tan solid (4.87 g, 63%); NMR Spectrum: 5.54 (s, 2H), 7.40 (dd, 1H), 7.56 (d, 1H), 7.69 (d, 1H), 7.89 (t, 1H), 8.47-8.51 (m, 2H), 8.60 (d, 1H), 10.44 (s, 1H); Mass Spectrum: 259 (MH+).

Provenance & Evidence