1-Naphthol → 2-[(Naphthalen-1-yl)oxy]-5-nitropyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 17.0 g. (0.107 mol.) of 2-chloro-5-nitro pyridine in 250 ml of DMF was added 15.4 g. (0.112 mol.) of potassium carbonate and 15.5 g. (0.107 mol.) of 1-naphthol. The resulting mixture was heated up to 125° C. for 3 hours. Additional potassium carbonate (1.5 g., 0.011 mol.) was added. This mixture was continued heating for 7 hours, cooled, and concentrated to give a black gummy product. It was then dissolved in 200 ml. of ethyl acetate. Florisil (60-100 mesh, 40 g.) was added to the above solution and the resulting mixture was concentrated to give brown powder. This material was packed on top of a column (450 g. florisil in hexane). Elution with hexane/ethyl acetate (96:4) gave 14.3 g. (0.054 mol., 50.3% of bright yellow crystals; mp. 87.3°-89.3° C.

Provenance & Evidence