Hydrochloric Acid → Sodium Methoxide

Participants

Reaction Steps

A solution of sodium methoxide is prepared by careful addition of sodium metal (13.6 g, 0.59 mol) to a flask containing methanol (500 ml) which is stirred. A solution of 5-carboxy-2-cyano-pyridine (36.0 g, 0.24 mol) in methanol (200 ml) is added to the sodium methoxide and the mixture heated for 2 h at 50°. After this time, freshly distilled ethylenediamine (28.8 g, 0.48 mol) and concentrated hydrochloric acid (64 ml) is added to the solution, which is then heated to 80° for 2.5 h. The reaction mixture is evaporated in vacuo to dryness. The residue is slurried in hot water (75 ml) for 15 min, filtered, washed with cold methanol (2×25 ml) and dried in vacuo at 60° to yield the title compound; m.p. 344°-345°.

Provenance & Evidence