Oxalic Acid → HCID 23047471, compound

Participants

Reaction Conditions

Reaction Steps

Propionamide oxime (440 mg; 5,0 mmol), dicyclohexylcarbodiimide (1030 mg; 5.0 mmol) and 4-carboxy-1-methyl-1,2,5,6-tetrahydropyridinium chloride (886 mg; 5,0 mmol) were mixed in distilled DMF. The mixture was stirred at 60° C. for 1 1/2 hours and evaporated in vacuo. To the residue was added water (50 ml) and the mixture was extracted with toluene (3×75 ml). pH was adjusted to 10 by means of 4N NaOH and extracted with toluene (3×100 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo. Upon dissolving the residue in ethanol (99.9%) (5 ml) a solution of oxalic acid (360 mg; 4,0 mmol) in ethanol (99,9%) (5 ml) was added. Crystallization gave the title compound in 15% yield. M.P. 170°-171° C.

Provenance & Evidence