Glyoxylic Acid → HCID 68773090, compound

Participants

Reaction Steps

The condensation of glyoxylic acid with the 2-acetylpyridine 4 is carried out according to an aldolization in a basic medium (potassium carbonate) (Scheme 3) (Coates and McKillop, 1992). This step was optimized from 31% to 65% by simply increasing the number of equivalents of the base to 3 eq., whereas the yield from this condensation drops in a more basic medium of potassium hydroxide (Coates and McKillop, 1992). The potassium 2-hydroxy-4-oxo-4-(pyridin-2-yl)butanoate 5 obtained subsequently becomes cyclized, at the reflux of acetic acid in the presence of hydrazine monohydrate, so as to form the intermediate 6 which becomes dehydrated in situ so as to give the 6-(pyridin-2-yl)-2H-pyridazin-3-one 7 with an overall yield of 65%.

Provenance & Evidence