Oxalic Acid → HCID 178483418, compound

Participants

Reaction Conditions

Reaction Steps

(4E)-N-Methyl-5-(6-hydroxy-3-pyridyl)-4-penten-2-amine (0.263 g of 91%, 1.23 mmol) was dissolved in warm absolute ethanol (3 mL) and combined with oxalic acid (0.110 g, 1.23 mmol) in warm absolute ethanol (4.5 mL). The solution was cooled at 4° C. for 1 h, during which time an oily material was deposited. The ethanol was evaporated to leave a dark brown oil, which was combined with 2-propanol (3 mL). This mixture (heterogeneous) was refluxed as absolute ethanol was added drop-wise. Once homogeneous, the mixture was cooled to ambient temperature as the walls of the flask were scratched with a spatula. A tan precipitate formed. The mixture was kept at 4° C. overnight and filtered. The filter cake was washed with cold 2-propanol and vacuum dried (40° C.) for 48 h. The resulting tan powder weighed 0.248 g (71% yield), mp 174-175.5° C.

Provenance & Evidence