p-Toluenesulfonic acid → HCID 43112089, compound

Participants

Reaction Conditions

Reaction Steps

Alternately, 3-pyridinecarboxaldehyde ((61.6 g, 0.575 moles, 1 eq) and methyl 4-aminobenzoate (1-03.87 g, 0.687 moles, 1.2 eq) with p-toluenesulfonic acid (2.19 g, 0.012 moles, 0.02 eq) were refluxed in methanol (25 volumes) for 2 hours. The reaction mixture was cooled to 0° C. and sodium borohydride (67.6 g, 1.787 moles, 3.5 eq) added slowly then it was allowed to warm to ambient overnight. The reaction was concentrated, dissolved with dichloromethane and washed with water then brine, and evaporated to give the title compound.

Provenance & Evidence